Organometallic compound, organic light-emitting device including the organometallic compound, and diagnostic composition including the organometallic compound

ABSTRACT

An organometallic compound represented by Formula 1, an organic light-emitting device including the organometallic compound, and a diagnostic composition including the organometallic compound:
 
M(L 1 ) n1 (L 2 ) n2 ,  Formula 1
         wherein, in Formula 1, M, L 1 , L 2 , n1, and n2 are each independently the same as described herein.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims the priority and the benefit of Korean PatentApplication No. 10-2019-0044480, filed on Apr. 16, 2019, in the KoreanIntellectual Property Office, and all the benefits accruing therefromunder 35 U.S.C. § 119, the contents of which in their entirety areherein incorporated by reference.

BACKGROUND 1. Field

An embodiment relates to an organometallic compound, an organiclight-emitting device including the organometallic compound, and adiagnostic composition including the organometallic compound.

2. Description of the Related Art

Organic light-emitting devices are self-emission devices, which haveexcellent characteristics in terms of a viewing angle, response time,brightness, driving voltage, and response speed, and produce full-colorimages.

In an example, an organic light-emitting device includes an anode, acathode, and an organic layer between the anode and the cathode, whereinthe organic layer includes an emission layer. A hole transport regionmay be between the anode and the emission layer, and an electrontransport region may be between the emission layer and the cathode.Holes provided from the anode may move toward the emission layer throughthe hole transport region, and electrons provided from the cathode maymove toward the emission layer through the electron transport region.The holes and the electrons recombine in the emission layer to produceexcitons. These excitons transit from an excited state to a groundstate, thereby generating light.

Luminescent compounds may be used to monitor, sense, or detect a varietyof biological materials including cells and proteins. An example of theluminescent compounds is a phosphorescent luminescent compound.

SUMMARY

Aspects of the present disclosure provide a novel organometalliccompound, an organic light-emitting device including the same, and adiagnostic composition including the novel organometallic compound.

Additional aspects will be set forth in part in the description whichfollows and, in part, will be apparent from the description, or may belearned by practice of the presented embodiments.

An aspect of the present disclosure provides an organometallic compoundrepresented by Formula 1 below:M(L₁)_(n1)(L₂)_(n2).  Formula 1

In Formula 1,

M may be a transition metal,

L₁ may be a ligand represented by Formula 2,

n1 may be 1, 2, or 3, wherein, when n1 is 2 or more, two or more L₁(s)may be identical to or different from each other,

L₂ may be a monodentate ligand, a bidentate ligand, a tridentate ligand,or a tetradentate ligand,

n2 may be 0, 1, 2, 3, or 4, wherein, when n2 is 2 or more, two or moreL₂(s) may be identical to or different from each other, and

L₁ and L₂ may be different from each other:

In Formula 2,

X₁ may be C, N, Si, or P,

X₂₁ may be C or N,

ring CY₁ and ring CY₂₁ may each independently be a C₅-C₃₀ carbocyclicgroup or a C₂-C₃₀ heterocyclic group,

X₂ and X₃ may each independently be O, S, Se, or C(R₂), wherein X₂ or X₃may be O, S, or Se,

X₄ may be N or C(R₄),

X₅ may be N or C(R₅),

R₁, R₂, R₄, R₅, and R₂₁ may each independently be hydrogen, deuterium,—F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro group,an amino group, an amidino group, a hydrazine group, a hydrazone group,a carboxylic acid group or a salt thereof, a sulfonic acid group or asalt thereof, a phosphoric acid group or a salt thereof, a substitutedor unsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstitutedC₂-C₆₀ alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynylgroup, a substituted or unsubstituted C₁-C₆₀ alkoxy group, a substitutedor unsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₂-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₂-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₇-C₆₀ arylalkyl group (e.g., a substituted orunsubstituted phenyl(C₁-C₂₀ alkyl) group), a substituted orunsubstituted heteroaryl group, a substituted or unsubstituted C₂-C₆₀heteroarylalkyl group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group, —N(Q₁)(Q₂),—Si(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), —P(═O)(Q₈)(Q₉) or —P(Q₈)(Q₉),

a1 and a21 may each independently be an integer from 0 to 20,

ring CY₁ and R₂ may not be linked to each other, and R₁ and R₂ may notbe linked to each other,

L₁₁ may be a C₅-C₃₀ carbocyclic group that is unsubstituted orsubstituted with at least one R_(10a) group or a C₂-C₃₀ heterocyclicgroup that is unsubstituted or substituted with at least one R_(10a)group,

b11 may be an integer from 0 to 10, wherein, when b11 is 0, a grouprepresented by *-(L₁₁)_(b11)-*′ may be a single bond, and when b11 is 2or more, two or more L₁₁(s) may be identical to or different from eachother,

two or more of a plurality of neighboring R₂₁(s) may optionally belinked to form a C₅-C₃₀ carbocyclic group that is unsubstituted orsubstituted with at least one R_(10a) group or a C₂-C₃₀ heterocyclicgroup that is unsubstituted or substituted with at least one R_(10a)group,

R_(10a) may be the same as defined in connection with R₂₁,

* and *′ each indicate a binding site to M in Formula 1,

a substituent(s) of the substituted C₅-C₃₀ carbocyclic group, thesubstituted C₂-C₃₀ heterocyclic group, the substituted C₁-C₆₀ alkylgroup, the substituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀alkynyl group, the substituted C₁-C₆₀ alkoxy group, the substitutedC₃-C₁₀ cycloalkyl group, the substituted C₂-C₁₀ heterocycloalkyl group,the substituted C₃-C₁₀ cycloalkenyl group, the substituted C₂-C₁₀heterocycloalkenyl group, the substituted C₆-C₆₀ aryl group, thesubstituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀ arylthio group,the substituted C₇-C₆₀ arylalkyl group (e.g., the substitutedphenyl(C₁-C₂₀ alkyl) group), the substituted C₂-C₆₀ heteroarylalkylgroup, the substituted heteroaryl group, the substituted monovalentnon-aromatic condensed polycyclic group, and the substituted monovalentnon-aromatic condensed heteropolycyclic group may be:

deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenylgroup, a C₂-C₆₀ alkynyl group, or a C₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, ora C₁-C₆₀ alkoxy group, each substituted with deuterium, —F, —Cl, —Br,—I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, aC₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₇-C₆₀arylalkyl group, a phenyl(C₁-C₂₀ alkyl) group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, amonovalent non-aromatic condensed heteropolycyclic group, —N(Q₁₁)(Q₁₂),—Si(Q₁₃)(Q₁₄)(Q₁₅), —B(Q₁₆)(Q₁₇), —P(═O)(Q₁₈)(Q₁₉), or any combinationthereof;

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₇-C₆₀arylalkyl group (e.g., a phenyl(C₁-C₂₀ alkyl) group), a C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, or amonovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₇-C₆₀arylalkyl group (e.g., a phenyl(C₁-C₂₀ alkyl) group), a C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, or amonovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃,—CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀ alkylgroup, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxygroup, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, aC₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₇-C₆₀arylalkyl group (e.g., a phenyl(C₁-C₂₀ alkyl) group), a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅), —B(Q₂₆)(Q₂₇), —P(═O)(Q₂₈)(Q₂₉), or anycombination thereof;

—N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), —B(Q₃₆)(Q₃₇), or —P(═O)(Q₃₈)(Q₃₉); orany combination thereof, and

Q₁ to Q₉, Q₁₁ to Q₁₉, Q₂₁ to Q₂₉, and Q₃₁ to Q₃₉ may each independentlybe hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryl groupsubstituted with a C₁-C₆₀ alkyl group, a C₆-C₆₀ aryl group, or anycombination thereof, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₇-C₆₀ arylalkyl group (e.g., a phenyl(C₁-C₂₀ alkyl) group), a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,or a monovalent non-aromatic condensed heteropolycyclic group.

Another aspect of the present disclosure provides an organiclight-emitting device including: a first electrode; a second electrode;and an organic layer between the first electrode and the secondelectrode and including an emission layer, wherein the organic layerincludes at least one organometallic compound represented by Formula 1.

The organometallic compound represented by Formula 1 included in theemission layer of the organic layer may act as a dopant.

Another aspect of the present disclosure provides a diagnosticcomposition including at least one organometallic compound representedby Formula 1.

BRIEF DESCRIPTION OF THE DRAWING

These and/or other aspects will become apparent and more readilyappreciated from the following description of the embodiments, taken inconjunction with FIGURE which is a schematic cross-sectional view of anorganic light-emitting device according to an embodiment.

DETAILED DESCRIPTION

Reference will now be made in detail to embodiments, examples of whichare illustrated in the accompanying drawings, wherein like referencenumerals refer to like elements throughout. In this regard, the presentembodiments may have different forms and should not be construed asbeing limited to the descriptions set forth herein. Accordingly, theembodiments are merely described below, by referring to the FIGURES, toexplain aspects of the present description. As used herein, the term“and/or” includes any and all combinations of one or more of theassociated listed items. Expressions such as “at least one of,” whenpreceding a list of elements, modify the entire list of elements and donot modify the individual elements of the list.

It will be understood that when an element is referred to as being “on”another element, it can be directly on the other element or interveningelements may be present therebetween. In contrast, when an element isreferred to as being “directly on” another element, there are nointervening elements present.

It will be understood that, although the terms “first,” “second,”“third” etc. may be used herein to describe various elements,components, regions, layers and/or sections, these elements, components,regions, layers and/or sections should not be limited by these terms.These terms are only used to distinguish one element, component, region,layer, or section from another element, component, region, layer, orsection. Thus, “a first element,” “component,” “region,” “layer,” or“section” discussed below could be termed a second element, component,region, layer, or section without departing from the teachings herein.

The terminology used herein is for the purpose of describing particularembodiments only and is not intended to be limiting. As used herein, thesingular forms “a,” “an,” and “the” are intended to include the pluralforms, including “at least one,” unless the content clearly indicatesotherwise. “At least one” is not to be construed as limiting “a” or“an.” “Or” means “and/or.” As used herein, the term “and/or” includesany and all combinations of one or more of the associated listed items.It will be further understood that the terms “comprises” and/or“comprising,” or “includes” and/or “including” when used in thisspecification, specify the presence of stated features, regions,integers, steps, operations, elements, and/or components, but do notpreclude the presence or addition of another feature, region, integer,step, operation, element, component, and/or groups thereof.

Furthermore, relative terms, such as “lower” or “bottom” and “upper” or“top,” may be used herein to describe one element's relationship toanother element as illustrated in the FIGURES. It will be understoodthat relative terms are intended to encompass different orientations ofthe device in addition to the orientation depicted in the FIGURES. Forexample, if the device in one of the FIGURES is turned over, elementsdescribed as being on the “lower” side of other elements would then beoriented on “upper” sides of the other elements. The exemplary term“lower,” can therefore, encompasses both an orientation of “lower” and“upper,” depending on the particular orientation of the FIGURE.Similarly, if the device in one of the FIGURES is turned over, elementsdescribed as “below” or “beneath” other elements would then be oriented“above” the other elements. The exemplary terms “below” or “beneath”can, therefore, encompass both an orientation of above and below.

“About” or “approximately” as used herein is inclusive of the statedvalue and means within an acceptable range of deviation for theparticular value as determined by one of ordinary skill in the art,considering the measurement in question and the error associated withmeasurement of the particular quantity (i.e., the limitations of themeasurement system). For example, “about” can mean within one or morestandard deviations, or within ±30%, 20%, 10%, or 5% of the statedvalue.

Unless otherwise defined, all terms (including technical and scientificterms) used herein have the same meaning as commonly understood by oneof ordinary skill in the art to which this disclosure belongs. It willbe further understood that terms, such as those defined in commonly useddictionaries, should be interpreted as having a meaning that isconsistent with their meaning in the context of the relevant art and thepresent disclosure, and will not be interpreted in an idealized oroverly formal sense unless expressly so defined herein.

Exemplary embodiments are described herein with reference to crosssection illustrations that are schematic illustrations of idealizedembodiments. As such, variations from the shapes of the illustrations asa result, for example, of manufacturing techniques and/or tolerances,are to be expected. Thus, embodiments described herein should not beconstrued as limited to the particular shapes of regions as illustratedherein but are to include deviations in shapes that result, for example,from manufacturing. For example, a region illustrated or described asflat may, typically, have rough and/or nonlinear features. Moreover,sharp angles that are illustrated may be rounded. Thus, the regionsillustrated in the figures are schematic in nature and their shapes arenot intended to illustrate the precise shape of a region and are notintended to limit the scope of the present claims.

An aspect of the present disclosure provides an organometallic compoundrepresented by Formula 1 below:M(L₁)_(n1)(L₂)_(n2).  Formula 1

M in Formula 1 may be a transition metal.

For example, M may be a first-row transition metal, a second-rowtransition metal, or a third-row transition metal of the Periodic Tableof Elements.

In an embodiment, M may be iridium (Ir), platinum (Pt), osmium (Os),titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium(Tb), thulium (Tm), or rhodium (Rh).

In an embodiment, M may be Ir, Pt, Os, or Rh, but embodiments of thepresent disclosure are not limited thereto.

L₁ in Formula 1 may be a ligand represented by Formula 2, and n1 inFormula 1 indicates the number of L₁ in Formula 1 and may be 1, 2, or 3.When n1 is 2 or more, two or more L₁(s) may be identical to or differentfrom each other:

Formula 2 may be the same as described below.

For example, n1 may be 1 or 2.

L₂ in Formula 1 may be a monodentate ligand, a bidentate ligand, atridentate ligand, or a tetradentate ligand, and n2 in Formula 1indicates the number of L₂ and may be 0, 1, 2, 3, or 4. When n2 is 2 ormore, two or more L₂(s) may be identical to or different from eachother. L₂ may be the same as described below.

For example, n2 in Formula 1 may be 1 or 2.

In Formula 1, L₁ and L₂ may be different from each other.

In an embodiment, M may be Ir or Os, and the sum of n1 and n2 may be 3or 4; or M may be Pt, and the sum of n1 and n2 may be 2.

In Formula 2, X₁ may be C, N, Si, or P, and X₂₁ may be C or N.

For example, in Formula 2, X₂₁ may be C.

In Formula 2, ring CY₁ and ring CY₂₁ may each independently be a C₅-C₃₀carbocyclic group or a C₂-C₃₀ heterocyclic group.

For example, ring CY₁ and ring CY₂₁ may each independently be i) a firstring, ii) a second ring, iii) a condensed ring in which at least twofirst rings are condensed with each other, iv) a condensed ring in whichat least two second rings are condensed with each other, or v) acondensed ring in which at least one first ring and at least one secondring are condensed with each other.

The first ring may be a cyclopentane group, a cyclopentadiene group, afuran group, a thiophene group, a pyrrole group, a silole group, anindene group, a benzofuran group, a benzothiophene group, an indolegroup, a benzosilole group, an oxazole group, an isoxazole group, anoxadiazole group, an isoxadiazole group, an oxatriazole group, anisoxatriazole group, a thiazole group, an isothiazole group, athiadiazole group, an isothiadiazole group, a thiatriazole group, anisothiatriazole group, a pyrazole group, an imidazole group, a triazolegroup, a tetrazole group, an azasilole group, a diazasilole group, or atriazasilole group.

The second ring may be an admantane group, a norbornane group, anorbornene group, a cyclohexane group, a cyclohexene group, a benzenegroup, a pyridine group, a pyrimidine group, a pyrazine group, apyridazine group, or a triazine group.

In an embodiment, ring CY₁ and ring CY₂₁ may each independently be acyclopentene group, a cyclohexene group, a benzene group, a naphthalenegroup, an anthracene group, a phenanthrene group, a triphenylene group,a pyrene group, a chrysene group, a cyclopentadiene group, a1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group,an indole group, a benzoborole group, a benzophosphole group, an indenegroup, a benzosilole group, a benzogermole group, a benzothiophenegroup, a benzoselenophene group, a benzofuran group, a carbazole group,a dibenzoborole group, a dibenzophosphole group, a fluorene group, adibenzosilole group, a dibenzogermole group, a dibenzothiophene group, adibenzoselenophene group, a dibenzofuran group, a dibenzothiophene5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxidegroup, an azaindole group, an azabenzoborole group, an azabenzophospholegroup, an azaindene group, an azabenzosilole group, an azabenzogermolegroup, an azabenzothiophene group, an azabenzoselenophene group, anazabenzofuran group, an azacarbazole group, an azadibenzoborole group,an azadibenzophosphole group, an azafluorene group, an azadibenzosilolegroup, an azadibenzogermole group, an azadibenzothiophene group, anazadibenzoselenophene group, an azadibenzofuran group, anazadibenzothiophene 5-oxide group, an aza-9H-fluorene-9-one group, anazadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidinegroup, a pyrazine group, a pyridazine group, a triazine group, aquinoline group, an isoquinoline group, a quinoxaline group, aquinazoline group, a phenanthroline group, a pyrrole group, a pyrazolegroup, an imidazole group, a triazole group, an oxazole group, anisoxazole group, a thiazole group, an isothiazole group, an oxadiazolegroup, a thiadiazole group, a benzopyrazole group, a benzimidazolegroup, a benzoxazole group, a benzothiazole group, a benzoxadiazolegroup, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group,or a 5,6,7,8-tetrahydroquinoline group, but embodiments of the presentdisclosure are not limited thereto.

In an embodiment, ring CY₁ may be a cyclopentane group, a cyclohexanegroup, a cycloheptane group, a cyclooctane group, an adamantane group, anorbornane group, a norbornene group, a cyclopentene group, acyclohexene group, a cycloheptene group, a benzene group, a naphthalenegroup, a fluorene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a pyrrole group, a thiophene group, a furan group, an imidazolegroup, a pyrazole group, a thiazole group, an isothiazole group, anoxazole group, an isoxazole group, a pyridine group, a pyrazine group, apyrimidine group, a pyridazine group, an isoindole group, an indolegroup, an indazole group, a purine group, a quinoline group, anisoquinoline group, a benzoquinoline group, a quinoxaline group, aquinazoline group, a cinnoline group, a carbazole group, aphenanthroline group, a benzimidazole group, a benzofuran group, abenzothiophene group, an isobenzothiazole group, a benzoxazole group, anisobenzoxazole group, a triazole group a tetrazole group, an oxadiazolegroup, a triazine group, a dibenzofuran group, a dibenzothiophene group,a dibenzosilole group, a benzocarbazole group, a dibenzocarbazole group,an imidazopyridine group, or an imidazopyrimidine group, but embodimentsof the present disclosure are not limited thereto.

In Formula 2, X₂ and X₃ may each independently be O, S, Se, or C(R₂),wherein X₂ or X₃ may be O, S, or Se.

For example, in Formula 2, i) X₂ may be O, S, or Se, and X₃ may beC(R₂); or ii) X₂ may be C(R₂), and X₃ may be O, S, or Se.

In Formula 2, X₄ may be N or C(R₄), and X₅ may be N or C(R₅).

For example, X₄ may be C(R₄), and X₅ may be C(R₅).

In Formula 2, R₁, R₂, R₄, R₅, R₂₁, and R_(10a) may each independently behydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₂-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₂-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₇-C₆₀ arylalkyl group (e.g., a substitutedor unsubstituted phenyl(C₁-C₂₀ alkyl) group), a substituted orunsubstituted C₁-C₆₀ heteroaryl group, substituted or unsubstitutedC₂-C₆₀ heteroarylalkyl group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group, —N(Q₁)(Q₂),—Si(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), —P(═O)(Q₈)(Q₉) or —P(Q₈)(Q₉), wherein Q₁ toQ₉ are each the same as described above.

For example, R₁, R₂, R₄, R₅, R₂₁, and R_(10a) may each independently be:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,—SF₅, a C₁-C₂₀ alkyl group, or a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group or a C₁-C₂₀ alkoxy group, each substituted withdeuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₁₀ alkyl group, a cyclopentyl group,a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, anadamantyl group, a norbornenyl group, a cyclopentenyl group, acyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group,a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, abicyclo[2.2.2]octyl group, a phenyl group, a biphenyl group, a terphenylgroup, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or anycombination thereof; a cyclopentyl group, a cyclohexyl group, acycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornenylgroup, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenylgroup, a cyclooctenyl group, a bicyclo[1.1.1]pentyl group, abicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, abicyclo[2.2.2]octyl group, a phenyl group, a biphenyl group, a terphenylgroup, a naphthyl group, a fluorenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group,a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolylgroup, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, an isoindolyl group, an indolyl group, an indazolyl group, apurinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthrolinyl group, abenzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinylgroup, or an imidazopyrimidinyl group, each unsubstituted or substitutedwith deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H,—CFH₂, a hydroxyl group, a cyano group, a nitro group, an amino group,an amidino group, a hydrazine group, a hydrazone group, a carboxylicacid group or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptylgroup, a cyclooctyl group, an adamantyl group, a norbornenyl group, acyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, acyclooctenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexylgroup, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, aphenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a pyrrolyl group, a thiophenyl group, a furanyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a pyridinyl group, apyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolylgroup, an indolyl group, an indazolyl group, a purinyl group, aquinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, an imidazopyridinyl group, animidazopyrimidinyl group, —Si(Q₃₃)(Q₃₄)(Q₃₅), or any combinationthereof; or

—N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), —P(═O)(Q₈)(Q₉), or —P(Q₈)(Q₉),and

Q₁ to Q₉ and Q₃₃ to Q₃₅ may each independently be:

—CH₃, —CD₃, —CD₂H, —CDH₂, —CH₂CH₃, —CH₂CD₃, —CH₂CD₂H, —CH₂CDH₂, —CHDCH₃,—CHDCD₂H, —CHDCDH₂, —CHDCD₃, —CD₂CD₃, —CD₂CD₂H, or —CD₂CDH₂; or ann-propyl group, an isopropyl group, an n-butyl group, an isobutyl group,a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentylgroup, a sec-pentyl group, a tert-pentyl group, a phenyl group, or anaphthyl group, each unsubstituted or substituted with deuterium, aC₁-C₁₀ alkyl group, a phenyl group, or any combination thereof, butembodiments of the present disclosure are not limited thereto.

In Formula 2, a1 and a21 each indicate the number of R₁ and the numberof R₂₁, respectively, and may each independently be an integer from 0 to20 (for example, an integer from 0 to 10 or an integer from 0 to 5).When a1 is 2 or more, two or more R₁(s) may be identical to or differentfrom each other, and when a21 is 2 or more, two or more R₂₁(s) may beidentical to or different from each other.

In Formula 2, ring CY₁ and R₂ are not linked to each other, and R₁ andR₂ are not linked to each other.

In an embodiment, a group represented by

in Formula 2 may be a C₅₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₃₀ aryl group, a C₂-C₃₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, or amonovalent non-aromatic condensed heteropolycyclic group, eachunsubstituted or substituted with R₁(s) in the number of a1.

In Formula 2, R₁ and R₂ may each independently be:

hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, or —SF₅; or

a C₁-C₆₀ alkyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group,a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, or aC₂-C₁₀ heterocycloalkenyl group, each unsubstituted or substituted withdeuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, acyano group, a C₁-C₂₀ alkyl group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclooctyl group, an adamantyl group, anorbornyl group, a norbornenyl group, a cyclopentenyl group, acyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenylgroup, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or anycombination thereof, and

a1 may be an integer from 0 to 10.

Detailed descriptions of a1, R₁, a C₁-C₆₀ alkyl group, a C₁-C₆₀ alkoxygroup, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, aC₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₃₀aryl group, a C₂-C₃₀ heteroaryl group, a monovalent non-aromaticcondensed polycyclic group, and a monovalent non-aromatic condensedheteropolycyclic group are the same as described above.

In an embodiment, a group represented by

in Formula 2 may be a phenyl group, a biphenyl group, a naphthyl group,a fluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a pyrrolyl group, a thiophenyl group, a furanyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a pyridinyl group, apyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolylgroup, an indolyl group, an indazolyl group, a purinyl group, aquinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, an imidazopyridinyl group, or animidazopyrimidinyl group, each unsubstituted or substituted with R₁(s)in the number of a1.

In Formula 2, R₁ and R₂ may each independently be:

hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, or —SF₅; or

a methyl group, an ethyl group, a propyl group, an n-butyl group, anisobutyl group, a sec-butyl group, a tert-butyl group, an n-pentylgroup, an isopentyl group, a sec-pentyl group, a tert-pentyl group, ann-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group,an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptylgroup, an n-octyl group, an isooctyl group, a sec-octyl group, atert-octyl group, an n-nonanyl group (an n-nonyl group), an isononanylgroup (an isononyl group), a sec-nonanyl group (a sec-nonyl group), atert-nonanyl group (a tert-nonyl group), an n-decanyl group, anisodecanyl group, a sec-decanyl group, a tert-decanyl group, a C₁-C₁₀alkoxy, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclooctyl group, an adamantyl group, a norbornyl group, a norbornenylgroup, a cyclopentenyl group, a cyclohexenyl group, or a cycloheptenylgroup, each unsubstituted or substituted with deuterium, —F, —Cl, —Br,—I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a cyano group, a C₁-C₂₀alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptylgroup, a cyclooctyl group, an adamantyl group, a norbornyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a biphenyl group, a naphthyl group,a pyridinyl group, a pyrimidinyl group, or any combination thereof, and

a1 may be an integer from 0 to 5, but embodiments of the presentdisclosure are not limited thereto.

In an embodiment, a group represented by

in Formula 2 may be a group represented by one of Formulae 10-13(1) to10-13(18) or 10-13:

In Formulae 10-13(1) to 10-13(18) and 10-13, R_(1a) to R_(1e) are eachindependently the same as defined in connection with R₁, wherein R_(1a)to R_(1e) are not each hydrogen, and * indicates a binding site to aneighboring atom (e.g., carbon atom).

For example, a group represented by

in Formula 2 may be a group represented by one of Formulae 10-13 to10-240, wherein R₁, R₂, R₄, R₅, R₂₁, and R_(10a) may each independentlybe hydrogen, deuterium, —F, a cyano group, a nitro group, —SF₅, —CH₃,—CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a group represented by one ofFormulae 9-1 to 9-19, a group represented by one of Formulae 10-1 to10-240, or —Si(Q₃)(Q₄)(Q₅) (wherein Q₃ to Q₅ are the same as describedabove), but embodiments of the present disclosure are not limitedthereto:

In Formulae 9-1 to 9-19 and 10-1 to 10-240, * indicates a binding siteto a neighboring atom, Ph indicates a phenyl group, and TMS indicates atrimethylsilyl group.

In Formula 2, L₁₁ may be a C₅-C₃₀ carbocyclic group that isunsubstituted or substituted with at least one R_(10a) or a C₂-C₃₀heterocyclic group that is unsubstituted or substituted with at leastone R_(10a), wherein R_(10a) is the same as described above.

For example, L₁₁ may be a benzene group, a naphthalene group, ananthracene group, a phenanthrene group, a triphenylene group, a pyrenegroup, a chrysene group, a cyclopentadiene group, a thiophene group, afuran group, an indole group, a benzoborole group, a benzophospholegroup, an indene group, a benzosilole group, a benzogermole group, abenzothiophene group, a benzoselenophene group, a benzofuran group, acarbazole group, a dibenzoborole group, a dibenzophosphole group, afluorene group, a dibenzosilole group, a dibenzogermole group, adibenzothiophene group, a dibenzoselenophene group, a dibenzofurangroup, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, adibenzothiophene 5,5-dioxide group, an azaindole group, anazabenzoborole group, an azabenzophosphole group, an azaindene group, anazabenzosilole group, an azabenzogermole group, an azabenzothiophenegroup, an azabenzoselenophene group, an azabenzofuran group, anazacarbazole group, an azadibenzoborole group, an azadibenzophospholegroup, an azafluorene group, an azadibenzosilole group, anazadibenzogermole group, an azadibenzothiophene group, anazadibenzoselenophene group, an azadibenzofuran group, anazadibenzothiophene 5-oxide group, an aza-9H-fluorene-9-one group, anazadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidinegroup, a pyrazine group, a pyridazine group, a triazine group, aquinoline group, an isoquinoline group, a quinoxaline group, aquinazoline group, a phenanthroline group, a pyrrole group, a pyrazolegroup, an imidazole group, a triazole group, an oxazole group, anisoxazole group, a thiazole group, an isothiazole group, an oxadiazolegroup, a thiadiazole group, a benzopyrazole group, a benzimidazolegroup, a benzoxazole group, a benzothiazole group, a benzoxadiazolegroup, or a benzothiadiazole group, each unsubstituted or substitutedwith at least one R_(10a) group, but embodiments of the presentdisclosure are not limited thereto.

In Formula 2, b11 indicates the number of L₁₁, and may be an integerfrom 0 to 10, wherein, when b11 is 0, a group represented by*-(L₁₁)_(b11)-*′ may be a single bond, and when b11 is 2 or more, two ormore L₁₁(s) may be identical to or different from each other. Forexample, b11 may be 0, 1, 2, or 3, but embodiments of the presentdisclosure are not limited thereto.

In Formula 2, two or more of a plurality of neighboring R₂₁(s) mayoptionally be linked to form a C₅-C₃₀ carbocyclic group that isunsubstituted or substituted with at least one R_(10a) group or a C₂-C₃₀heterocyclic group that is unsubstituted or substituted with at leastone R_(10a) group (for example, a benzene group, a cyclopentane group, acyclopentadiene group, a furan group, a thiophene group, a pyrrolegroup, a silole group, an indene group, a benzofuran group, abenzothiophene group, an indole group, or a benzosilole group, eachunsubstituted or substituted with at least one R_(10a) group), whereinR_(10a) is the same as defined in connection with R₂₁. Detaileddescriptions of a C₅-C₃₀ carbocyclic group and a C₂-C₃₀ heterocyclicgroup are the same as described above.

In Formula 2, * and *′ each indicate a binding site to M in Formula 1.

In an embodiment, a group represented by

in Formula 2 may be a group represented by one of Formulae CY21-1 toCY21-25:

In Formulae CY21-1 to CY21-25,

X₂₁ and R₂₁ may each independently be the same as described herein,

X₂₂ may be C(R₂₂)(R₂₃), N(R₂₂), O, S, or Si(R₂₂)(R₂₃),

R₂₂ to R₂₉ may each independently be the same as defined in connectionwith R₂₁,

a26 may be an integer from 0 to 6,

a24 may be an integer from 0 to 4,

a23 may be an integer from 0 to 3,

a22 may be an integer from 0 to 2,

*″ indicates a binding site to a carbon atom of a neighboring 6-memberedring in Formula 2, and

* indicates a binding site to M in Formula 1.

In an embodiment, a group represented by

in Formula 2 may be a group represented by one of Formulae CY21(1) toCY21(56) or a group represented by one of Formulae CY21-20 to CY21-25:

In Formulae CY21(1) to CY21(56),

X₂₁ and R₂₁ may each independently be the same as described herein,

R_(21a) to R_(21d) may each independently be the same as defined inconnection with R₂₁, wherein R₂₁ and R_(21a) to R_(21d) are not eachhydrogen,

*″ indicates a binding site to a carbon atom of a neighboring 6-memberedring in Formula 2, and

* indicates a binding site to M in Formula 1.

In an embodiment, a group represented by

in Formula 2 may be a group represented by one of Formulae CY21(1),CY21(3), or CY21(10) or a group represented by one of Formulae CY21-20to CY21-25, but embodiments of the present disclosure are not limitedthereto. For example, in Formula CY21(10), R_(21a) and R_(21b) may beidentical to or different from each other. In an embodiment, in FormulaCY21(10), R_(21a) and R_(21b) may be different from each other, and thenumber of carbon atoms included in R_(21a) may be larger than the numberof carbon atoms included in R_(21b).

In an embodiment, in Formula 1, L₁ may be a ligand represented byFormula 2A or 2B, but embodiments of the present disclosure are notlimited thereto:

In Formulae 2A and 2B, X₁, X₂₁, ring CY₁, ring CY₂₁, X₄, X₅, R₁, R₂,R₂₁, a1, a21, L₁₁, b11, *, and *′ may each independently be the same asdescribed herein, wherein X₂ and X₃ may each independently be O, S, orSe.

In Formula 1, L₂ may be a bidentate ligand linked to M of Formula 1 viaO, S, N, C, P, Si, or As.

In an embodiment, in Formula 1, L₂ may be a bidentate ligand representedby Formula 3:

In Formula 3,

X₃₁ and X₃₂ may each independently be O, S, N, C, P, Si, or As,

indicates an arbitrary atom group linking X₃₁ and X₃₂ to each other, and

* and *′ each indicate a binding site to M in Formula 1.

For example, in Formula 3, i) X₃₁ and X₃₂ may each be O; ii) X₃₁ may beO, and X₃₂ may be N, or iii) X₃₁ may be N, and X₃₂ may be C, butembodiments of the present disclosure are not limited thereto.

In an embodiment, in Formula 1, L₂ may be a monodentate ligand, forexample, I⁻, Br⁻, C₁ ⁻, sulfide, nitrate, azide, hydroxide, cyanate,isocyanate, thiocyanate, water, acetonitrile, pyridine, ammonia, carbonmonoxide, P(Ph)₃, P(Ph)₂CH₃, PPh(CH₃)₂, P(CH₃)₃, or any combinationthereof, but embodiments of the present disclosure are not limitedthereto.

In an or more embodiment, in Formula 1, L₂ may be a bidentate ligand,for example, oxalate, acetylacetonate, picolinic acid,1,2-bis(diphenylphosphino)ethane, 1,1-bis(diphenylphosphino)methane,glycinate, ethylenediamine, or any combination thereof, but embodimentsof the present disclosure are not limited thereto.

In an or more embodiment, in Formula 1, L₂ may be a group represented byone of Formulae 3A to 3F:

In Formulae 3A to 3F,

Y₁₃ may be O, N, N(Z₁), P(Z₁)(Z₂), or As(Z₁)(Z₂),

Y₁₄ may be O, N, N(Z₃), P(Z₃)(Z₄), or As(Z₃)(Z₄),

T₁₁ may each independently be a single bond, a double bond,*—C(Z₁₁)(Z₁₂)—*′, *—C(Z₁₁)═C(Z₁₂)—*′, *═C(Z₁₁)—*′, *—C(Z₁₁)═*′,*═C(Z₁₁)—C(Z₁₂)═C(Z₁₃)—*′, *—C(Z₁₁)═C(Z₁₂)—C(Z₁₃)═*′, *—N(Z₁₁)—*′, or aC₅-C₃₀ carbocyclic group that is unsubstituted or substituted with atleast one Z₁₁ group,

a11 may be an integer from 1 to 10,

Y₁₁ and Y₁₂ may each independently be C or N,

T₂₁ may be a single bond, a double bond, O, S, C(Z₁₁)(Z₁₂),Si(Z₁₁)(Z₁₂), or N(Z₁₁),

ring CY₁₁ and ring CY₁₂ may each independently be a C₅-C₃₀ carbocyclicgroup or a C₂-C₃₀ heterocyclic group,

A₁ may be P or As,

Z₁ to Z₄ and Z₁₁ to Z₁₃ may each independently be the same as defined inconnection with R₂₁,

d1 and d2 may each independently be an integer from 0 to 10, and

* and *′ each indicate a binding site to M in Formula 1.

In Formulae 3A to 3F, the C₅-C₃₀ carbocyclic group and the C₂-C₃₀heterocyclic group may each independently be the same as defined inconnection with ring CY₂₁.

For example, a moiety represented by

in Formula 3D may be a group represented by one of Formulae CY11-1 toCY11-34, and/or

a moiety represented by

in Formulae 3C and 3D may be a group represented by one of FormulaeCY12-1 to CY12-34:

In Formulae CY11-1 to CY11-34 and CY12-1 to CY12-34,

X₃₁ may be O, S, N(Z₁₁), C(Z₁₁)(Z₁₂), or Si(Z₁₁)(Z₁₂),

X₄₁ may be O, S, N(Z₂₁), C(Z₂₁)(Z₂₂), or Si(Z₂₁)(Z₂₂),

Y₁₁, Y₁₂, Z₁, and Z₂ may each independently be the same as describedherein,

Z₁₁ to Z₁₈ and Z₂₁ to Z₂₈ may each independently be the same as definedin connection with R₂₁,

d12 and d22 may each independently be an integer from 0 to 2,

d13 and d23 may each independently be an integer from 0 to 3,

d14 and d24 may each independently be an integer from 0 to 4,

d15 and d25 may each independently be an integer from 0 to 5,

d16 and d26 may each independently be an integer from 0 to 6, and

in Formulae CY11-1 to CY11-34 and CY12-1 to CY12-34, * and *′ eachindicate a binding site to M in Formula 1, and *″ indicates a bindingsite to a neighboring atom in Formula 3C or a binding site to T₂₁ inFormula 3D.

In an embodiment, in Formula 1, L₂ may be a group represented by one ofFormulae 3-1(1) to 3-1(66) or one of 3-1(301) to 3-1(309), butembodiments of the present disclosure are not limited thereto:

In Formulae 3-1(1) to 3-1(66) and 3-1(301) to 3-1(309),

X₄₁ may be O, S, N(Z₂₁), C(Z₂₁)(Z₂₂), or Si(Z₂₁)(Z₂₂),

Z₁ to Z₄, Z_(1a), Z_(1b), Z_(1c), Z_(1d), Z_(2a), Z_(2b), Z_(2c),Z_(2d), Z₁₁ to Z₁₄, Z₂₁ and Z₂₂ may each independently be the same asdefined in connection with R₂₁,

d14 may be an integer from 0 to 4,

d26 may be an integer from 0 to 6, and

* and *′ each indicate a binding site to M in Formula 1.

In an embodiment, the organometallic compound represented by Formula 1may emit red light or green light. In an embodiment, the organometalliccompound represented by Formula 1 may emit red light or green light,each having a maximum emission wavelength of about 500 nm or more, forexample, about 500 nm or more and about 650 nm or less.

The terms “an azaindole group, an azabenzoborole group, anazabenzophosphole group, an azaindene group, an azabenzosilole group, anazabenzogermole group, an azabenzothiophene group, anazabenzoselenophene group, an azabenzofuran group, an azacarbazolegroup, an azadibenzoborole group, an azadibenzophosphole group, anazafluorene group, an azadibenzosilole group, an azadibenzogermolegroup, an azadibenzothiophene group, an azadibenzoselenophene group, anazadibenzofuran group, an azadibenzothiophene 5-oxide group, anaza-9H-fluorene-9-one group, and an azadibenzothiophene 5,5-dioxidegroup” as used herein each refer to a heterocyclic group having the samebackbone as “an indole group, a benzoborole group, a benzophospholegroup, an indene group, a benzosilole group, a benzogermole group, abenzothiophene group, a benzoselenophene group, a benzofuran group, acarbazole group, a dibenzoborole group, a dibenzophosphole group, afluorene group, a dibenzosilole group, a dibenzogermole group, adibenzothiophene group, a dibenzoselenophene group, a dibenzofurangroup, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, anda dibenzothiophene 5,5-dioxide group” in which at least one carbon atomconstituting the cyclic groups is substituted with N.

In an embodiment, the organometallic compound represented by Formula 1may be one of Compounds 1 to 420, but embodiments of the presentdisclosure are not limited thereto:

L₁ of the organometallic compound represented by Formula 1 may be aligand represented by Formula 2, and n1 which indicates the number of L₁may be 1, 2, or 3. That is, the organometallic compound essentiallyincludes, as ligands linked to metal M, at least one ligand representedby Formula 2.

X₂ and X₃ in the ligand represented by Formula 2 are each independentlyO, S, Se, or C(R₂), wherein X₂ or X₃ is O, S, or Se. That is, in Formula2, the 5-membered ring (see Formula 2′) does not include *═N—*′ (* and*′ each indicate a binding site to a neighboring atom) as a ring-formingatom, and includes O, S, or Se. In addition, in Formula 2, the5-membered ring is condensed with the 6-membered ring while sharingcarbon 1 and carbon 2 (see Formula 2′). A reduction in theintermolecular bonding force of the organometallic compound representedby Formula 1 may be prevented. Therefore, a reduction in the lifespan ofan electronic device, for example, an organic light-emitting device,which includes the organometallic compound represented by Formula 1, maybe prevented.

The ligand represented by Formula 2 includes “ring CY₁”. Therefore, atransition dipole moment increases in an alignment axis direction ofFormula 1, and the alignment of the organometallic compound representedby Formula 1 may be improved, thereby increasing the luminescenceefficiency of an electronic device, for example, an organiclight-emitting device, which includes the organometallic compoundrepresented by Formula 1.

Meanwhile, in Formula 2, ring CY₁ and R₂ are not linked to each other,and R₁ and R₂ are not linked to each other. Therefore, it is possible toprevent a transition dipole moment of Formula 1 from deviating to adirection other than the alignment axis direction of Formula 1, therebyincreasing the luminescence efficiency of an electronic device, forexample, an organic light-emitting device, which includes theorganometallic compound represented by Formula 1.

A highest occupied molecular orbital (HOMO) energy level, a lowestunoccupied molecular orbital (LUMO) energy level, and a triplet (Ti)energy level of some compounds of the organometallic compoundrepresented by Formula 1 are evaluated by a density functional theory(DFT) of Gaussian program with molecular structure optimization based onB3LYP, and results are shown in Table 1.

TABLE 1 Compound HOMO LUMO T₁ No. (eV) (eV) (eV)    16 −4.542 −1.6942.008 101 −4.749 −1.682 2.177 116 −4.600 −1.671 2.081 146 −4.687 −1.6512.150 216 −4.576 −1.747 2.075 316 −4.633 −1.747 2.116

Referring to Table 1, it is confirmed that the organometallic compoundrepresented by Formula 1 has such electrical characteristics that aresuitable for use in an electronic device, for example, an organiclight-emitting device, for use as a dopant.

Synthesis methods of the organometallic compound represented by Formula1 may be understood by one of ordinary skill in the art by referring toSynthesis Examples provided below.

Therefore, the organometallic compound represented by Formula 1 may besuitable for use in an organic layer of an organic light-emittingdevice, for example, for use as a dopant in an emission layer of theorganic layer. Another aspect of the present disclosure provides anorganic light-emitting device including: a first electrode, a secondelectrode, and an organic layer disposed between the first electrode andthe second electrode and including an emission layer, wherein theorganic layer includes at least one organometallic compound representedby Formula 1.

The organic light-emitting device may have, due to the inclusion of anorganic layer including the organometallic compound represented byFormula 1, a low driving voltage, high external quantum luminescenceefficiency, a low roll-off ratio, and a long lifespan.

The organometallic compound represented by Formula 1 may be used betweena pair of electrodes of an organic light-emitting device. For example,the organometallic compound represented by Formula 1 may be included inthe emission layer. In this regard, the organometallic compound may actas a dopant, and the emission layer may further include a host (that is,an amount of the organometallic compound represented by Formula 1 issmaller than an amount of the host). The emission layer may emit, forexample, green light or red light.

The expression “(an organic layer) includes at least one organometalliccompound represented by Formula 1” as used herein may include a case inwhich “(an organic layer) includes identical organometallic compoundsrepresented by Formula 1” and a case in which “(an organic layer)includes two or more different organometallic compounds represented byFormula 1”.

For example, the organic layer may include, as the organometalliccompound represented by Formula 1, only Compound 1. In this regard,Compound 1 may exist only in the emission layer of the organiclight-emitting device. In an embodiment, the organic layer may include,as the organometallic compound represented by Formula 1, Compound 1 andCompound 2. In this regard, Compound 1 and Compound 2 may exist in anidentical layer (for example, Compound 1 and Compound 2 all may exist inan emission layer).

The first electrode may be an anode, which is a hole injectionelectrode, and the second electrode may be a cathode, which is anelectron injection electrode; or the first electrode may be a cathode,which is an electron injection electrode, and the second electrode maybe an anode, which is a hole injection electrode.

For example, the organic light-emitting device, the first electrode isan anode, and the second electrode is a cathode, and the organic layerfurther includes a hole transport region disposed between the firstelectrode and the emission layer and an electron transport regiondisposed between the emission layer and the second electrode, and thehole transport region includes a hole injection layer, a hole transportlayer, an electron blocking layer, or any combination thereof, and theelectron transport region includes a hole blocking layer, an electrontransport layer, an electron injection layer, or any combinationthereof.

The term “organic layer” as used herein refers to a single layer and/ora plurality of layers disposed between the first electrode and thesecond electrode of an organic light-emitting device. The “organiclayer” may include, in addition to an organic compound, anorganometallic complex including metal.

FIGURE is a schematic cross-sectional view of an organic light-emittingdevice 10 according to an embodiment. Hereinafter, the structure of anorganic light-emitting device according to an embodiment and a method ofmanufacturing an organic light-emitting device according to anembodiment will be described in connection with the FIGURE. The organiclight-emitting device 10 includes a first electrode 11, an organic layer15, and a second electrode 19, which are sequentially stacked.

A substrate may be additionally disposed under the first electrode 11 orabove the second electrode 19. For use as the substrate, any substratethat is used in the organic light-emitting device art may be used, andthe substrate may be a glass substrate or a transparent plasticsubstrate, each having excellent mechanical strength, thermal stability,transparency, surface smoothness, ease of handling, and waterresistance.

The first electrode 11 may be formed by depositing or sputtering amaterial for forming the first electrode 11 on the substrate. The firstelectrode 11 may be an anode. The material for forming the firstelectrode 11 may be a material with a high work function to facilitatehole injection. The first electrode 11 may be a reflective electrode, asemi-reflective electrode, or a transmissive electrode. The material forforming the first electrode may be, for example, indium tin oxide (ITO),indium zinc oxide (IZO), tin oxide (SnO₂), or zinc oxide (ZnO). In anembodiment, the material for forming the first electrode 11 may be ametal or a metal alloy, such as magnesium (Mg), aluminum (Al),aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), ormagnesium-silver (Mg—Ag).

The first electrode 11 may have a single-layered structure or amulti-layered structure including two or more layers. For example, thefirst electrode 11 may have a three-layered structure of ITO/Ag/ITO, butthe structure of the first electrode 11 is not limited thereto.

The organic layer 15 is disposed on the first electrode 11.

The organic layer 15 may include a hole transport region, an emissionlayer, and an electron transport region.

The hole transport region may be disposed between the first electrode 11and the emission layer.

The hole transport region may include a hole injection layer, a holetransport layer, an electron blocking layer, a buffer layer, or anycombination thereof.

The hole transport region may include only either a hole injection layeror a hole transport layer. In an embodiment, the hole transport regionmay have a hole injection layer/hole transport layer structure or a holeinjection layer/hole transport layer/electron blocking layer structure,which are sequentially stacked in this stated order from the firstelectrode 11.

When the hole transport region includes a hole injection layer, the holeinjection layer may be formed on the first electrode 11 by using asuitable method, for example, vacuum deposition, spin coating, casting,and/or Langmuir-Blodgett (LB) deposition.

When a hole injection layer is formed by vacuum deposition, thedeposition conditions may vary according to a material that is used toform the hole injection layer, and the structure and thermalcharacteristics of the hole injection layer. For example, the depositionconditions may include a deposition temperature of about 100° C. toabout 500° C., a vacuum pressure of about 10⁻⁸ torr to about 10⁻³ torr,and a deposition rate of about 0.01 Å/sec to about 100 Å/sec. However,the deposition conditions are not limited thereto.

When the hole injection layer is formed using spin coating, coatingconditions may vary according to the material used to form the holeinjection layer, and the structure and thermal properties of the holeinjection layer. For example, a coating speed may be from about 2,000rpm to about 5,000 rpm, and a temperature at which a heat treatment isperformed to remove a solvent after coating may be from about 80° C. toabout 200° C. However, the coating conditions are not limited thereto.

Conditions for forming a hole transport layer and an electron blockinglayer may be understood by referring to conditions for forming the holeinjection layer.

The hole transport region may include, for example, m-MTDATA, TDATA,2-TNATA, NPB, β-NPB, TPD, spiro-TPD, spiro-NPB, methylated-NPB, TAPC,HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA),polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonic acid (PANI/CSA),polyaniline/poly(4-styrenesulfonate) (PANI/PSS), a compound representedby Formula 201 below, a compound represented by Formula 202 below, orany combination thereof:

In Formula 201, Ar₁₀₁ and Ar₁₀₂ may each independently be a phenylenegroup, a pentalenylene group, an indenylene group, a naphthylene group,an azulenylene group, a heptalenylene group, an acenaphthylene group, afluorenylene group, a phenalenylene group, a phenanthrenylene group, ananthracenylene group, a fluoranthenylene group, a triphenylenylenegroup, a pyrenylene group, a chrysenylene group, a naphthacenylenegroup, a picenylene group, a perylenylene group, or a pentacenylenegroup, each unsubstituted or substituted with deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkylgroup, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₇-C₆₀ arylalkyl group (e.g.,a phenyl(C₁-C₂₀ alkyl) group), a C₁-C₆₀ heteroaryl group, a C₂-C₆₀heteroarylalkyl group, a monovalent non-aromatic condensed polycyclicgroup, a monovalent non-aromatic condensed heteropolycyclic group, orany combination thereof.

In Formula 201, xa and xb may each independently be an integer from 0 to5, or may be 0, 1, or 2. For example, xa may be 1, and xb may be 0, butembodiments of the present disclosure are not limited thereto.

In Formulae 201 and 202, R₁₀₁ to R₁₀₈, R₁₁₁ to R₁₁₉, and R₁₂₁ to R₁₂₄may each independently be:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₁₀ alkyl group (for example, a methyl group, an ethyl group, apropyl group, a butyl group, pentyl group, a hexyl group, and the like),or a C₁-C₁₀ alkoxy group (for example, a methoxy group, an ethoxy group,a propoxy group, a butoxy group, a pentoxy group, and the like);

a C₁-C₁₀ alkyl group or a C₁-C₁₀ alkoxy group, each substituted withdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, or anycombination thereof; or

a phenyl group, a naphthyl group, an anthracenyl group, a fluorenylgroup, or a pyrenyl group, each unsubstituted or substituted withdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀alkyl group, a C₁-C₁₀ alkoxy group, or any combination thereof,

but embodiments of the present disclosure are not limited thereto.

In Formula 201, R₁₀₉ may be a phenyl group, a naphthyl group, ananthracenyl group, or a pyridinyl group, each unsubstituted orsubstituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, anaphthyl group, an anthracenyl group, a pyridinyl group, or anycombination thereof.

In an embodiment, the compound represented by Formula 201 may berepresented by Formula 201A below, but embodiments of the presentdisclosure are not limited thereto:

Detailed descriptions of R₁₀₁, R₁₁₁, R₁₁₂, and R₁₀₉ in Formula 201A arethe same as described above.

For example, the compound represented by Formula 201, and the compoundrepresented by Formula 202 may include Compounds HT1 to HT20 but are notlimited thereto:

A thickness of the hole transport region may be from about 100 Å toabout 10,000 Å, for example, about 100 Å to about 1,000 Å. When the holetransport region includes a hole injection layer, a hole transportlayer, or any combination thereof, a thickness of the hole injectionlayer may be in a range of about 100 Å to about 10,000 Å, for example,about 100 Å to about 1,000 Å, and a thickness of the hole transportlayer may be in a range of about 50 Å to about 2,000 Å, for exampleabout 100 Å to about 1,500 Å. When the thicknesses of the hole transportregion, the hole injection layer, and the hole transport layer arewithin these ranges, satisfactory hole transporting characteristics maybe obtained without a substantial increase in driving voltage.

The hole transport region may further include, in addition to thesematerials, a charge-generation material for the improvement ofconductive properties. The charge-generation material may behomogeneously or non-homogeneously dispersed in the hole transportregion.

The charge-generation material may be, for example, a p-dopant. Thep-dopant may be a quinone derivative, a metal oxide, a cyanogroup-containing compound, or any combination thereof, but embodimentsof the present disclosure are not limited thereto. Non-limiting examplesof the p-dopant are a quinone derivative, such astetracyanoquinodimethane (TCNQ) or2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ); ametal oxide, such as a tungsten oxide or a molybdenum oxide; and a cyanogroup-containing compound, such as Compound HT-D1 below, but are notlimited thereto:

The hole transport region may include a buffer layer.

Also, the buffer layer may compensate for an optical resonance distanceaccording to a wavelength of light emitted from the emission layer, andthus, efficiency of a formed organic light-emitting device may beimproved.

Meanwhile, when the hole transport region includes an electron blockinglayer, a material for the electron blocking layer may be materials forthe hole transport region described above, materials for a host to beexplained later, or any combination thereof. However, the material forthe electron blocking layer is not limited thereto. For example, whenthe hole transport region includes an electron blocking layer, amaterial for the electron blocking layer may be mCP, which will beexplained later.

Then, an emission layer may be formed on the hole transport region byvacuum deposition, spin coating, casting, LB deposition, or the like.When the emission layer is formed by vacuum deposition or spin coating,the deposition or coating conditions may be similar to those applied informing the hole injection layer although the deposition or coatingconditions may vary according to a compound that is used to form theemission layer.

The emission layer may include a host and a dopant, and the dopant mayinclude the organometallic compound represented by Formula 1.

The host may include TPBi, TBADN, ADN (also referred to as “DNA”), CBP,CDBP, TCP, mCP, one of Compounds H50 to H52, or any combination thereof:

When the organic light-emitting device is a full-color organiclight-emitting device, the emission layer may be patterned into a redemission layer, a green emission layer, and/or a blue emission layer. Inan embodiment, due to a stacked structure including a red emissionlayer, a green emission layer, and/or a blue emission layer, theemission layer may emit white light.

When the emission layer includes a host and a dopant, an amount of thedopant may be in a range of about 0.01 parts by weight to about 15 partsby weight based on 100 parts by weight of the host, but embodiments ofthe present disclosure are not limited thereto.

A thickness of the emission layer may be in a range of about 100 Å toabout 1,000 Å, for example, about 200 Å to about 600 Å. When thethickness of the emission layer is within this range, excellentlight-emission characteristics may be obtained without a substantialincrease in driving voltage.

Then, an electron transport region may be disposed on the emissionlayer.

The electron transport region may include a hole blocking layer, anelectron transport layer, an electron injection layer, or anycombination thereof.

For example, the electron transport region may have a hole blockinglayer/electron transport layer/electron injection layer structure, or anelectron transport layer/electron injection layer structure, but thestructure of the electron transport region is not limited thereto. Theelectron transport layer may have a single-layered structure or amulti-layered structure including two or more different materials.

Conditions for forming the hole blocking layer, the electron transportlayer, and the electron injection layer which constitute the electrontransport region may be understood by referring to the conditions forforming the hole injection layer.

When the electron transport region includes a hole blocking layer, thehole blocking layer may include, for example, BCP, Bphen, BAlq, or anycombination thereof, but embodiments of the present disclosure are notlimited thereto:

A thickness of the hole blocking layer may be from about 20 Å to about1,000 Å, for example, about 30 Å to about 300 Å. When the thickness ofthe hole blocking layer is within these ranges, the hole blocking layermay have excellent hole blocking characteristics without a substantialincrease in driving voltage.

The electron transport layer may include BCP, Bphen, Alq₃, BAlq, TAZ,NTAZ, or any combination thereof:

In an embodiment, the electron transport layer may include one of ET1 toET25, but embodiments of the present disclosure are not limited thereto:

A thickness of the electron transport layer may be from about 100 Å toabout 1,000 Å, for example, about 150 Å to about 500 Å. When thethickness of the electron transport layer is within the range describedabove, the electron transport layer may have satisfactory electrontransport characteristics without a substantial increase in drivingvoltage.

Also, the electron transport layer may further include, in addition tothe materials described above, a metal-containing material.

The metal-containing material may include a Li complex. The Li complexmay include, for example, Compound ET-D1 (LiQ), ET-D2, or anycombination thereof:

The electron transport region may include an electron injection layerthat promotes flow of electrons from the second electrode 19 thereinto.

The electron injection layer may include LiF, NaCl, CsF, Li₂O, BaO, orany combination thereof.

A thickness of the electron injection layer may be from about 1 Å toabout 100 Å, for example, about 3 Å to about 90 Å. When a thickness ofthe electron injection layer is within these ranges, satisfactoryelectron injection characteristics may be obtained without substantialincrease in driving voltage.

The second electrode 19 is disposed on the organic layer 15. The secondelectrode 19 may be a cathode. A material for forming the secondelectrode 19 may be a metal, an alloy, an electrically conductivecompound, or any combination thereof, which have a relatively low workfunction. For example, lithium (Li), magnesium (Mg), aluminum (Al),aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), ormagnesium-silver (Mg—Ag) may be used as the material for forming thesecond electrode 19. To manufacture a top-emission type light-emittingdevice, a transmissive electrode formed using ITO or IZO may be used asthe second electrode 19.

Hereinbefore, the organic light-emitting device according to anembodiment has been described in connection with the FIGURE.

Another aspect of the present disclosure provides a diagnosticcomposition including at least one organometallic compound representedby Formula 1.

The organometallic compound represented by Formula 1 provides highluminescence efficiency. Accordingly, a diagnostic composition includingthe organometallic compound may have high diagnostic efficiency.

The diagnostic composition may be used in various applications includinga diagnosis kit, a diagnosis reagent, a biosensor, and a biomarker.

The term “C₁-C₆₀ alkyl group” as used herein refers to a linear orbranched saturated aliphatic hydrocarbon monovalent group having 1 to 60carbon atoms, and examples thereof include a methyl group, an ethylgroup, a propyl group, an isobutyl group, a sec-butyl group, atert-butyl group, a pentyl group, an isoamyl group, and a hexyl group.The term “C₁-C₆₀ alkylene group” as used herein refers to a divalentgroup having the same structure as the C₁-C₆₀ alkyl group.

The term “C₁-C₆₀ alkoxy group” as used herein refers to a monovalentgroup represented by —OA₁₀₁ (wherein A₁₀₁ is the C₁-C₆₀ alkyl group),and examples thereof include a methoxy group, an ethoxy group, and anisopropyloxy group.

The term “C₂-C₆₀ alkenyl group” as used herein refers to a hydrocarbongroup having at least one carbon-carbon double bond in the middle or atthe terminus of the C₂-C₆₀ alkyl group, and examples thereof include anethenyl group, a propenyl group, and a butenyl group. The term “C₂-C₆₀alkenylene group” as used herein refers to a divalent group having thesame structure as the C₂-C₆₀ alkenyl group.

The term “C₂-C₆₀ alkynyl group” as used herein refers to a hydrocarbongroup having at least one carbon-carbon triple bond in the middle or atthe terminus of the C₂-C₆₀ alkyl group, and examples thereof include anethynyl group, and a propynyl group. The term “C₂-C₆₀ alkynylene group”as used herein refers to a divalent group having the same structure asthe C₂-C₆₀ alkynyl group.

The term “C₃-C₁₀ cycloalkyl group” as used herein refers to a monovalentsaturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, andnon-limiting examples thereof include a cyclopropyl group, a cyclobutylgroup, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.The term “C₃-C₁₀ cycloalkylene group” as used herein refers to adivalent group having the same structure as the C₃-C₁₀ cycloalkyl group.

The term “C₂-C₁₀ heterocycloalkyl group” as used herein refers to amonovalent saturated monocyclic group having N, O, P, Si, Se, S, or acombination thereof and 2 to 10 carbon atoms as ring-forming atoms, andnon-limiting examples thereof include a tetrahydrofuranyl group and atetrahydrothiophenyl group. The term “C₂-C₁₀ heterocycloalkylene group”as used herein refers to a divalent group having the same structure asthe C₂-C₁₀ heterocycloalkyl group.

The term “C₃-C₁₀ cycloalkenyl group” as used herein refers to amonovalent monocyclic group that has 3 to 10 carbon atoms and at leastone carbon-carbon double bond in the ring thereof and no aromaticity,and non-limiting examples thereof include a cyclopentenyl group, acyclohexenyl group, and a cycloheptenyl group. The term “C₃-C₁₀cycloalkenylene group” as used herein refers to a divalent group havingthe same structure as the C₃-C₁₀ cycloalkenyl group.

The term “C₂-C₁₀ heterocycloalkenyl group” as used herein refers to amonovalent monocyclic group that has N, O, P, Si, Se, S, or anycombination thereof and 2 to 10 carbon atoms as ring-forming atoms, andat least one double bond in its ring. Examples of the C₂-C₁₀heterocycloalkenyl group are a 2,3-dihydrofuranyl group, and a2,3-dihydrothiophenyl group. The term “C₂-C₁₀ heterocycloalkenylenegroup” as used herein refers to a divalent group having the samestructure as the C₂-C₁₀ heterocycloalkenyl group.

The term “C₆-C₆₀ aryl group” as used herein refers to a monovalent grouphaving a carbocyclic aromatic system having 6 to 60 carbon atoms, andthe term “C₆-C₆₀ arylene group” as used herein refers to a divalentgroup having a carbocyclic aromatic system having 6 to 60 carbon atoms.Non-limiting examples of the C₆-C₆₀ aryl group include a phenyl group, anaphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenylgroup, and a chrysenyl group. When the C₆-C₆₀ aryl group and the C₆-C₆₀arylene group each include two or more rings, the rings may be fused toeach other.

The term “C₇-C₆₀ arylalkyl group” as used herein refers to an alkylenegroup substituted with an aryl group. A non-limiting example of a C₇-C₆₀arylalkyl group includes a —CH₂-phenyl (i.e., benzyl) group and aCH₂-naphthyl group.

The term “phenyl(C₁-C₂₀ alkyl) group” as used herein refers to analkylene group substituted with a phenyl group. Non-limiting examples ofa phenyl(C₁-C₂₀ alkyl) group include a —CH₂-phenyl (i.e., benzyl) groupand a (CH₂)₃-phenyl group.

The term “C₁-C₆₀ heteroaryl group” as used herein refers to a monovalentgroup having a heterocyclic aromatic system that has N, O, P, Si, Se, S,or any combination thereof and 1 to 60 carbon atoms as ring-formingatoms. The term “C₁-C₆₀ heteroarylene group” as used herein refers to adivalent group having a heterocyclic aromatic system that has N, O, P,Si, Se, S, or any combination thereof and 1 to 60 carbon atoms asring-forming atoms. Non-limiting examples of the C₁-C₆₀ heteroaryl groupinclude a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, apyridazinyl group, a triazinyl group, a quinolinyl group, and anisoquinolinyl group. When the C₁-C₆₀ heteroaryl group and the C₁-C₆₀heteroarylene group each include two or more rings, the rings may befused to each other.

The term “C₂-C₆₀ heteroarylalkyl group” as used herein refers to analkylene group substituted with a heteroaryl group. A non-limitingexample of a C₂-C₆₀ heteroarylalkyl group includes a —CH₂-pyridyl group.

The term “C₆-C₆₀ aryloxy group” as used herein indicates —OA₁₀₂ (whereinA₁₀₂ is the C₆-C₆₀ aryl group), and the term “C₆-C₆₀ arylthio group” asused herein indicates —SA₁₀₃ (wherein A₁₀₃ is the C₆-C₆₀ aryl group).

The term “monovalent non-aromatic condensed polycyclic group” as usedherein refers to a monovalent group (for example, having 8 to 60 carbonatoms) having two or more rings condensed to each other, only carbonatoms as ring-forming atoms, and no aromaticity in its entire molecularstructure. Examples of the monovalent non-aromatic condensed polycyclicgroup include a fluorenyl group. The term “divalent non-aromaticcondensed polycyclic group” as used herein refers to a divalent grouphaving the same structure as the monovalent non-aromatic condensedpolycyclic group.

The term “monovalent non-aromatic condensed heteropolycyclic group” asused herein refers to a monovalent group (for example, having 2 to 60carbon atoms) having two or more rings condensed to each other, aheteroatom selected from N, O, P, Si, and S, other than carbon atoms, asa ring-forming atom, and no aromaticity in its entire molecularstructure. Non-limiting examples of the monovalent non-aromaticcondensed heteropolycyclic group include a carbazolyl group. The term“divalent non-aromatic condensed heteropolycyclic group” as used hereinrefers to a divalent group having the same structure as the monovalentnon-aromatic condensed heteropolycyclic group.

The term “C₅-C₃₀ carbocyclic group” as used herein refers to a saturatedor unsaturated cyclic group having, as a ring-forming atom, 5 to 30carbon atoms only. The C₅-C₃₀ carbocyclic group may be a monocyclicgroup or a polycyclic group.

The term “C₂-C₃₀ heterocyclic group” as used herein refers to asaturated or unsaturated cyclic group having N, O, Si, P, Se, S, or anycombination thereof and 1 to 30 carbon atoms as ring-forming atoms. TheC₂-C₃₀ heterocyclic group may be a monocyclic group or a polycyclicgroup.

A substituent of the substituted C₅-C₃₀ carbocyclic group, thesubstituted C₂-C₃₀ heterocyclic group, the substituted C₁-C₆₀ alkylgroup, the substituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀alkynyl group, the substituted C₁-C₆₀ alkoxy group, the substitutedC₃-C₁₀ cycloalkyl group, the substituted C₂-C₁₀ heterocycloalkyl group,the substituted C₃-C₁₀ cycloalkenyl group, the substituted C₂-C₁₀heterocycloalkenyl group, the substituted C₆-C₆₀ aryl group, thesubstituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀ arylthio group,the substituted C₇-C₆₀ arylalkyl group (e.g., the substitutedphenyl(C₁-C₂₀ alkyl) group), the substituted C₁-C₆₀ heteroaryl group,the substituted C₂-C₆₀ heteroarylalkyl group, the substituted monovalentnon-aromatic condensed polycyclic group, and the substituted monovalentnon-aromatic condensed heteropolycyclic group may be:

deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenylgroup, a C₂-C₆₀ alkynyl group, or a C₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, ora C₁-C₆₀ alkoxy group, each substituted with deuterium, —F, —Cl, —Br,—I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, aC₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₇-C₆₀arylalkyl group (e.g., a phenyl(C₁-C₂₀ alkyl) group), a C₁-C₆₀heteroaryl group, C₂-C₆₀ heteroarylalkyl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅),—B(Q₁₆)(Q₁₇), —P(═O)(Q₁₈)(Q₁₉), or any combination thereof;

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₇-C₆₀ arylalkyl group (e.g., a phenyl(C₁-C₂₀ alkyl) group), aC₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroarylgroup, a C₂-C₆₀ heteroarylalkyl group, a monovalent non-aromaticcondensed polycyclic group, or a monovalent non-aromatic condensedheteropolycyclic group; a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₇-C₆₀ arylalkyl group (e.g., a phenyl(C₁-C₂₀alkyl) group), a C₆₀ heteroaryl group, C₂-C₆₀ heteroarylalkyl group, amonovalent non-aromatic condensed polycyclic group, or a monovalentnon-aromatic condensed heteropolycyclic group, each substituted withdeuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₆₀ alkyl group, a C₂-C₆₀ alkenyl group,a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkylgroup, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₇-C₆₀ arylalkylgroup (e.g., a phenyl(C₁-C₂₀ alkyl) group), a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, C₂-C₆₀ heteroarylalkylgroup, a monovalent non-aromatic condensed polycyclic group, amonovalent non-aromatic condensed heteropolycyclic group, —N(Q₂₁)(Q₂₂),—Si(Q₂₃)(Q₂₄)(Q₂₅), —B(Q₂₆)(Q₂₇), —P(═O)(Q₂₈)(Q₂₉), or any combinationthereof;

—N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), —B(Q₃₆)(Q₃₇), or —P(═O)(Q₃₈)(Q₃₉); or

any combination thereof.

In the present specification, Q₁ to Q₉, Q₁₁ to Q₁₉, Q₂₁ to Q₂₉, and Q₃₁to Q₃₉ may each independently be hydrogen, deuterium, —F, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenylgroup, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryl group substituted with a C₁-C₆₀ alkyl group, a C₆-C₆₀ aryl group,or any combination thereof, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthiogroup, a C₇-C₆₀ arylalkyl group (e.g., a phenyl(C₁-C₂₀ alkyl) group), aC₁-C₆₀ heteroaryl group, C₂-C₆₀ heteroarylalkyl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, or any combination thereof.

Hereinafter, a compound and an organic light-emitting device accordingto embodiments are described in detail with reference to SynthesisExample and Examples. However, the organic light-emitting device is notlimited thereto. The wording “B was used instead of A” used indescribing Synthesis Examples means that an amount of A used wasidentical to an amount of B used, in terms of a molar equivalent.

EXAMPLES Synthesis Example 1 (Compound 1)

Synthesis of Intermediate L1

6-Chloro-2-phenylfuro[2,3-b]pyridine (2.55 g, 11.1 mmol), phenylboronicacid (2.603 g, 16.64 mmol), Pd(PPh₃)₄ (1.03 g, 0.89 mmol), and K₂CO₃(3.83 g, 27.7 mmol) were mixed with 60 mL of tetrahydrofuran and 30 mLof distilled water, stirred at a temperature of 90° C. for 18 hours, andthen cooled to room temperature. An organic layer was extracted from aresult obtained therefrom by using ethyl acetate, dried by usinganhydrous magnesium sulfate (MgSO₄), and filtered to obtain a filtrate.The filtrate was concentrated to obtain a residue. The residue waspurified by column chromatography using ethyl acetate:hexane=1:2 (v/v)as an eluent to obtain Intermediate L1 (2.85 g, 83%).

LC-MS m/z=272 (M+H)⁺.

Synthesis of Intermediate L1-Dimer

Intermediate L1 (1.99 g, 7.32 mmol) and iridium chloride hydrate (1.15g, 3.25 mmol) were mixed with 21 mL of 2-ethoxyethanol and 7 mL ofdistilled water, stirred at a temperature of 120° C. for 24 hours underreflux, and then cooled to room temperature. A solid obtained therefromwas filtered, separated, and sufficiently washed in the order ofwater/methanol/hexane. The solid was dried in a vacuum oven to obtainIntermediate L1-dimer (1.95 g, 78%). The obtained compound was used inthe next reaction without additional purification.

Synthesis of Compound 1

Thirty mL of 2-ethoxyethanol was added to Intermediate L1-dimer (1.94 g,1.26 mmol), acetyl acetone (1.26 g, 12.6 mmol), and Na₂CO₃ (1.33 g, 12.6mmol), and stirred at room temperature for 12 hours. An organic layerwas extracted from a result obtained therefrom by using ethyl acetate,dried by using anhydrous magnesium sulfate (MgSO₄), and filtered toobtain a filtrate. The filtrate was concentrated to obtain a residue.The residue was purified by column chromatography usingdichloromethane:hexane=1:4 (v/v) as an eluent to obtain Compound 1(0.451 g, 22%). The obtained compound was identified by Massspectroscopy (MS) and HPLC analysis.

HRMS(MALDI-TOF) calcd for C₄₃H₃₁IrN₂O₄: m/z 832.1913, Found: 832.1913.

Synthesis Example 2 (Compound 16)

Synthesis of Intermediate L16

6-Chloro-2-phenylfuro[2,3-b]pyridine (2.69 g, 11.71 mmol),(3,5-dimethylphenyl)boronic acid (2.64 g, 17.56 mmol), Pd(PPh₃)₄ (1.08g, 0.94 mmol), and K₂CO₃ (4.05 g, 29.3 mmol) were mixed with 60 mL oftetrahydrofuran and 30 mL of distilled water, stirred at a temperatureof 90° C. for 18 hours, and then cooled to room temperature. An organiclayer was extracted from a result obtained therefrom by using ethylacetate, dried by using anhydrous magnesium sulfate (MgSO₄), andfiltered to obtain a filtrate. The filtrate was concentrated to obtain aresidue. The residue was purified by column chromatography using ethylacetate:hexane=1:2 (v/v) as an eluent to obtain Intermediate L16 (1.97g, 56%).

LC-MS m/z=300 (M+H)⁺.

Synthesis of Intermediate L16-dimer

Intermediate L16 (1.97 g, 6.82 mmol) and iridium chloride hydrate (1.07g, 3.03 mmol) were mixed with 21 mL of ethoxyethanol and 7 mL ofdistilled water, stirred at a temperature of 120° C. for 24 hours underreflux, and then cooled to room temperature. A solid obtained therefromwas filtered, separated, and sufficiently washed in the order ofwater/methanol/hexane. The solid was dried in a vacuum oven to obtainIntermediate L16-dimer (2.16 g, 86%). The obtained compound was used ina next reaction without additional purification.

Synthesis of Compound 16

Thirty mL of 2-ethoxyethanol was added to Intermediate L16-dimer (2.15g, 1.31 mmol), acetyl acetone (1.31 g, 13.1 mmol), and Na₂CO₃ (1.38 g,13.1 mmol), and stirred at room temperature for 12 hours. An organiclayer was extracted from a result obtained therefrom by using ethylacetate, dried by using anhydrous magnesium sulfate (MgSO₄), andfiltered to obtain a filtrate. The filtrate was concentrated to obtain aresidue. The residue was purified by column chromatography usingdichloromethane:hexane=1:4 (v/v) as an eluent to obtain Compound 16(0.47 g, 20%). The obtained compound was identified by MS and HPLCanalysis.

HRMS(MALDI-TOF) calcd for C₄₇H₃₉IrN₂O₄: m/z 888.2539, Found: 888.2538.

Synthesis Example 3 (Compound 101)

Synthesis of Intermediate L101

Intermediate L101 (2.08 g, 59%) was obtained in the same manner as inSynthesis of Intermediate L1 of Synthesis Example 1, except that6-chloro-2-phenylthieno[2,3-b]pyridine (2.99 g, 12.2 mmol) was usedinstead of 6-chloro-2-phenylfuro[2,3-b]pyridine (2.55 g, 11.1 mmol).

LC-MS m/z=288 (M+H)⁺.

Synthesis of Intermediate L101-dimer

Intermediate L101-dimer (2.16 g, 86%) was obtained in the same manner asin Synthesis of Intermediate L1-dimer of Synthesis Example 1, exceptthat Intermediate L101 (1.97 g, 7.03 mmol) was used instead ofIntermediate L1.

Synthesis of Compound 101

Compound 101 (0.47 g, 22%) was obtained in the same manner as inSynthesis of Compound 1 of Synthesis Example 1, except that IntermediateL101-dimer (1.95 g, 1.22 mmol) was used instead of IntermediateL1-dimer. The obtained compound was identified by MS and HPLC analysis.

HRMS(MALDI-TOF) calcd for C₄₃H₃₀IrN₂O₂S₂: m/z 863.1378, Found: 863.1377.

Synthesis Example 4 (Compound 116)

Synthesis of Intermediate L116

Intermediate L116 (3.00 g, 86%) was obtained in the same manner as inSynthesis of Intermediate L16 of Synthesis Example 2, except that6-chloro-2-phenylthieno[2,3-b]pyridine (2.73 g, 11.1 mmol) was usedinstead of 6-chloro-2-phenylfuro[2,3-b]pyridine (2.69 g, 11.71 mmol).

LC-MS m/z=316 (M+H)⁺.

Synthesis of Intermediate L116-dimer

Intermediate L116-dimer (2.16 g, 72%) was obtained in the same manner asin Synthesis of Intermediate L16-dimer of Synthesis Example 2, exceptthat Intermediate L116 (2.48 g, 7.88 mmol) was used instead ofIntermediate L16.

Synthesis of Compound 116

Compound 116 (0.47 g, 21%) was obtained in the same manner as inSynthesis of Compound 16 of Synthesis Example 2, except thatIntermediate L116-dimer (2.04 g, 1.19 mmol) was used instead ofIntermediate L16-dimer. The obtained compound was identified by MS andHPLC analysis.

HRMS(MALDI-TOF) calcd for C₄₇H₃₉IrN₂O₂ S₂: m/z 920.2082, Found:920.2080.

Synthesis Example 5 (Compound 146)

Synthesis of Intermediate L146

Intermediate L146 (3.30 g, 83%) was obtained in the same manner as inSynthesis of Intermediate L116 of Synthesis Example 4, except that(3-(tert-butyl)-5-methylphenyl)boronic acid (3.23 g, 16.8 mmol) was usedinstead of (3,5-dimethylphenyl)boronic acid (2.64 g, 17.56 mmol).

LC-MS m/z=358 (M+H)⁺.

Synthesis of Intermediate L146-dimer

Intermediate L146-dimer (2.60 g, 74%) was obtained in the same manner asin Synthesis of Intermediate L116-dimer of Synthesis Example 4, exceptthat Intermediate L146 (2.99 g, 8.37 mmol) was used instead ofIntermediate L116.

Synthesis of Compound 146

Compound 146 (0.48 g, 20%) was obtained in the same manner as inSynthesis of Compound 116 of Synthesis Example 4, except thatIntermediate L146-dimer (2.04 g, 1.19 mmol) was used instead ofIntermediate L116-dimer. The obtained compound was identified by MS andHPLC analysis.

HRMS(MALDI-TOF) calcd for C₄₇H₃₈IrN₂O₂ S₂: m/z 919.2004, Found:919.2003.

Synthesis Example 6 (Compound 216)

Synthesis of Intermediate L216

Intermediate L216 (3.00 g, 86%) was obtained in the same manner as inSynthesis of Intermediate L16 of Synthesis Example 2, except that5-chloro-2-phenylfuro[3,2-b]pyridine (2.69 g, 11.71 mmol) was usedinstead of 6-chloro-2-phenylfuro[2,3-b]pyridine (2.69 g, 11.71 mmol).

LC-MS m/z=300 (M+H)⁺.

Synthesis of Intermediate L216-dimer

Intermediate L216-dimer (3.2 g, 91%) was obtained in the same manner asin Synthesis of Intermediate L16-dimer of Synthesis Example 2, exceptthat Intermediate L216 (2.86 g, 9.55 mmol) was used instead ofIntermediate L16. The obtained compound was used in a next reactionwithout additional purification.

Synthesis of Compound 216

Compound 216 (0.75 g, 34%) was obtained in the same manner as inSynthesis of Compound 16 of Synthesis Example 2, except thatIntermediate L216-dimer (2.04 g, 1.24 mmol) was used instead ofIntermediate L16-dimer. The obtained compound was identified by MS andHPLC analysis.

HRMS(MALDI-TOF) calcd for C₄₇H₃₉IrN₂O₄: m/z 888.2539, Found: 888.2539.

Synthesis Example 7 (Compound 316)

Synthesis of Intermediate L316

Intermediate L316 (3.01 g, 76%) was obtained in the same manner as inSynthesis of Intermediate L16 of Synthesis Example 2, except that5-chloro-2-phenylthieno[3,2-b]pyridine (3.12 g, 12.7 mmol) was usedinstead of 5-chloro-2-phenylfuro[2,3-c]pyridine (2.69 g, 11.71 mmol).

LC-MS m/z=316 (M+H)⁺.

Synthesis of Intermediate L316-dimer

Intermediate L316-dimer (2.60 g, 74%) was obtained in the same manner asin Synthesis of Intermediate L16-dimer of Synthesis Example 2, exceptthat Intermediate L316 (2.89 g, 9.19 mmol) was used instead ofIntermediate L16.

Synthesis of Compound 316

Compound 316 (0.49 g, 20%) was obtained in the same manner as inSynthesis of Compound 16 of Synthesis Example 2, except thatIntermediate L316-dimer (2.23 g, 1.30 mmol) was used instead ofIntermediate L16-dimer. The obtained compound was identified by MS andHPLC analysis.

HRMS(MALDI-TOF) calcd for C₄₇H₃₉IrN₂O₂ S₂: m/z 920.2082, Found:920.2080.

Evaluation Example 1: Evaluation of Radiative Decay Rate

CBP and Compound 16 were co-deposited at a weight ratio of 9:1 under avacuum pressure of 10⁻⁷ torr to manufacture a film having a thickness of40 nm.

A PL spectrum of the film was evaluated at room temperature by using aPicoQuant TRPL measurement system FluoTime 300 and a PicoQuant pumpingsource PLS340 (excitation wavelength=340 nm, spectral width=20 nm), awavelength of a main peak of the spectrum was determined, and PLS340repeatedly measured the number of photons emitted from the film at thewavelength of the main peak due to a photon pulse (pulse width=500 ps)applied to the film according to time based on time-correlated singlephoton counting (TCSPC), thereby obtaining a sufficiently fittable TRPLcurve. A decay time T_(decay) of the film was obtained by fitting one ormore exponential decay functions to the result obtained therefrom. Thefunction used for fitting is expressed by Equation 10, and the greatestvalue among the values obtained from each exponential decay functionused for fitting was taken as T_(decay). At this time, a baseline orbackground signal curve was obtained by repeating the same measurementonce more for the same measurement time as the measurement time forobtaining the TRPL curve in a dark state (a state in which a pumpingsignal applied to the predetermined film was blocked), and the baselineor background signal curve was used for fitting as a baseline.

$\begin{matrix}{{f(t)} = {\sum\limits_{i = 1}^{n}{A_{i}{\exp( {{- t}/T_{{decay},i}} )}}}} & {{Equation}\mspace{14mu} 10}\end{matrix}$

Then, the quantum efficiency of the film was measured by using aHamamatsu Quantaurus-QY Absolute PL quantum yield spectrometer (providedwith a xenon light source, a monochromator, a photonic multichannelanalyzer, and an integrating sphere and using PLQY measurement software(Hamamatsu Photonics, Ltd., Shizuoka, Japan)). Upon measurement of thequantum efficiency, the excitation wavelength was measured whilescanning from 320 nm to 380 nm at an interval of 10 nm, and the greatestvalue was taken as the quantum efficiency (Φ).

The radiative decay rate (k_(r)) of Compound 1 was obtained bysubstituting T_(decay) and Φ into Equation 11, and results thereof areshown in Table 2.k _(r) =Φ/T _(decay)  Equation 11

The measurement of the radiative decay rate was repeated on Compounds101, 116, 146, 216, 316, A1, A2, B, C1, C2 and D, and results thereofare shown in Table 2.

TABLE 2 Radiative Compound decay No. rate (s⁻¹)    16 4.72 × 10⁵ 1015.68 × 10⁵ 116 7.09 × 10⁵ 146 6.72 × 10⁵ 216 1.22 × 10⁶ 316 1.56 × 10⁶A1 4.08 × 10⁵ A2 4.15 × 10⁵ B  4.62 × 10⁵ C1 1.85 × 10⁵ C2 3.52 × 10⁵ D 2.13 × 10⁵

From Table 2, it is confirmed that Compounds 16, 101, 116, 146, 216, and316 have high radiative decay rates, as compared with those of CompoundsA1, A2, B, C1, C2, and D.

Example 1

As an anode, a glass substrate, on which ITO/Ag/ITO were deposited tothicknesses of 70 Å/1,000 Å/70 Å, was cut to a size of 50 mm×50 mm×0.5mm, sonicated with isopropyl alcohol and pure water each for 5 minutes,and then cleaned by exposure to ultraviolet rays and ozone for 30minutes. Then, the glass substrate was provided to a vacuum depositionapparatus.

2-TNATA was vacuum-deposited on the anode to form a hole injection layerhaving a thickness of 600 Å, and4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) wasvacuum-deposited on the hole injection layer to form a hole transportlayer having a thickness of 1,350 Å.

Then, CBP (host) and Compound 16 (dopant) were co-deposited on the holetransport layer at a weight ratio of 98:2 to form an emission layerhaving a thickness of 400 Å.

Then, BCP was vacuum-deposited on the emission layer to form a holeblocking layer having a thickness of 50 Å, Alq₃ was vacuum-deposited onthe hole blocking layer to form an electron transport layer having athickness of 350 Å, LiF was vacuum-deposited on the electron transportlayer to form an electron injection layer having a thickness of 10 Å,and Mg and Ag were co-deposited on the electron injection layer at aweight ratio of 90:10 to form a cathode having a thickness of 120 Å,thereby completing the manufacture of an organic light-emitting device(which emits red light).

Examples 2 to 6 and Comparative Examples A1, A2, B, C1, C2, and D

Organic light-emitting devices were manufactured in the same manner asin Example 1, except that Compounds shown in Table 3 were each usedinstead of Compound 16 as a dopant in forming an emission layer.

Evaluation Example 2: Evaluation of Characteristics of OrganicLight-Emitting Devices

The driving voltage, maximum value of external quantum efficiency (MaxEQE), roll-off ratio, maximum emission wavelength of main peak of ELspectrum, and lifespan (T₉₇) of the organic light-emitting devicesmanufactured according to Examples 1 to 6 and Comparative Examples A1,A2, B, C1, C2, and D were evaluated, and results thereof are shown inTable 3. A current-voltage meter (Keithley 2400) and a luminance meter(Minolta Cs-1000A) were used as the evaluation devices, and the lifespan(T₉₇) (at 3,500 nit) indicates an amount of time that lapsed whenluminance was 97% of initial luminance (100%). The roll-off ratio wascalculated by Equation 20:Roll off ratio={1−(efficiency(at 3,500 nit)/maximum luminescenceefficiency)}×100%  Equation 20

TABLE 3 Compound No. of Roll- Maximum T₉₇ dopant in Driving Max Offemission (hr) (at emission voltage EQE ratio wavelength 3,500 layer (V)(%) (%) (nm) nit) Example 1  16 3.74 26.5 10 606 144 Example 2 101 3.6426.9 11 555 107 Example 3 116 3.74 27.6 10 581 157 Example 4 146 4.1726.4 11 557 156 Example 5 216 4.28 27.9  5 581 181 Example 6 316 4.2031.5  2 576 258 Comparative A1 5.75 24.1 19 575  85 Example A1Comparative A2 5.84 24.7 14 614  86 Example A2 Comparative B  4.3  26.012 580  60 Example B Comparative C1 5.22 24.4 32 514  48 Example C1Comparative C2 5.59 25.4 15 505  48 Example C2 Comparative D  4.34 24.628 555  69 Example D

From Table 3, it is confirmed that the organic light-emitting devices ofExamples 1 to 6 emit red light and have improved driving voltage,improved external quantum efficiency, improved roll-off ratio, andimproved lifespan characteristics, compared with those of the organiclight-emitting devices of Comparative Examples A1, A2, B, C1, C2, and D.

Since the organometallic compound has a high radiative decay rate, anelectronic device, for example, an organic light-emitting device, whichincludes the organometallic compound represented by Formula 1, may haveimproved driving voltage, improved external quantum luminescenceefficiency, improved roll-off ratio, and improved lifespancharacteristics. In addition, since the organometallic compound hasexcellent phosphorescent luminescent characteristics, a diagnosticcomposition having high diagnostic efficiency may be provided by usingthe organometallic compound.

It should be understood that embodiments described herein should beconsidered in a descriptive sense only and not for purposes oflimitation. Descriptions of features or aspects within each embodimentshould typically be considered as available for other similar featuresor aspects in other embodiments.

While embodiments have been described with reference to the FIGURES, itwill be understood by those of ordinary skill in the art that variouschanges in form and details may be made therein without departing fromthe spirit and scope as defined by the following claims.

What is claimed is:
 1. An organometallic compound represented by Formula1:M(L₁)_(n1)(L₂)_(n2),  Formula 1 wherein, in Formula 1, M is Ir or Os,and the sum of n1 and n2 is 3 or 4; or M is Pt, and the sum of n1 and n2is 2, L₁ is a ligand represented by Formula 2, n1 is 1, 2, or 3,wherein, when n1 is 2 or more, two or more Li are identical to ordifferent from each other, L₂ is a monodentate ligand, a bidentateligand, a tridentate ligand, or a tetradentate ligand, n2 is 0, 1, 2, 3,or 4, wherein, when n2 is 2 or more, two or more L₂ are identical to ordifferent from each other, and L₁ and L₂ are different from each other:

wherein, in Formula 2, X₁ is C or N X₂₁ is C or N, a group representedby

in Formula 2 is a phenyl group, a biphenyl group, a naphthyl group, afluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a pyrrolyl group, a thiophenyl group, a furanyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a pyridinyl group, apyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolylgroup, an indolyl group, an indazolyl group, a purinyl group, aquinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, an imidazopyridinyl group, or animidazopyrimidinyl group, each unsubstituted or substituted with R₁ inthe number of a1, a group represented by

in Formula 2 is a group represented by one of Formulae CY21-1 toCY21-25:

wherein, in Formulae CY21-1 to CY21-25, X₂₁ is C or N, X₂₂ isC(R₂₂)(R₂₃), N(R₂₂), O, S, or Si(R₂₂)(R₂₃), R₂₁ to R₂₉ are eachindependently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a substituted or unsubstituted C₁-C₆₀ alkylgroup, a substituted or unsubstituted C₂-C₆₀ alkenyl group, asubstituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₂-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₂-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₇-C₆₀ arylalkylgroup, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, asubstituted or unsubstituted C₂-C₆₀ heteroarylalkyl group, a substitutedor unsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropoly cyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇),—P(═O)(Q₈)(Q₉) or —P(Q₈)(Q₉), a26 is an integer from 0 to 6, a24 is aninteger from 0 to 4, a23 is an integer from 0 to 3, a22 is an integerfrom 0 to 2, *″ indicates a binding site to a carbon atom of aneighboring 6-membered ring in Formula 2, and * indicates a binding siteto M in Formula 1, X₂ and X₃ are each independently O, S, Se, or C(R₂),wherein one of X₂ or X₃ is O, S, or Se, X₄ is N or C(R₄), X₅ is N orC(R₅), R₁, R₂, R₄, and R₅ are each independently hydrogen, deuterium,—F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro group,an amino group, an amidino group, a hydrazine group, a hydrazone group,a carboxylic acid group or a salt thereof, a sulfonic acid group or asalt thereof, a phosphoric acid group or a salt thereof, a substitutedor unsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstitutedC₂-C₆₀ alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynylgroup, a substituted or unsubstituted C₁-C₆₀ alkoxy group, a substitutedor unsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₂-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₂-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₇-C₆₀ arylalkyl group, a substituted or unsubstitutedC₁-C₆₀ heteroaryl group, a substituted or unsubstituted C₂-C₆₀heteroarylalkyl group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group, —N(Q₁)(Q₂),—Si(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), —P(═O)(Q₈)(Q₉) or —P(Q₈)(Q₉), a1 is aninteger from 0 to 20, ring CY₁ and R₂ are not linked to each other, andR₁ and R₂ are not linked to each other, b11 is 0, wherein, when b11 is0, a group represented by *-(L₁₁)_(b11)-*′ is a single bond, two or moreof a plurality of neighboring R₂₁ are optionally linked to form a C₅-C₃₀carbocyclic group that is unsubstituted or substituted with at least oneR_(10a) groups or a C₂-C₃₀ heterocyclic group that is unsubstituted orsubstituted with at least one R_(10a) group, R_(10a) is the same asdefined in connection with R₂₁, * and *′ each indicate a binding site toM in Formula 1, a substituent of the substituted C₅-C₃₀ carbocyclicgroup, the substituted C₂-C₃₀ heterocyclic group, the substituted C₁-C₆₀alkyl group, the substituted C₂-C₆₀ alkenyl group, the substitutedC₂-C₆₀ alkynyl group, the substituted C₁-C₆₀ alkoxy group, thesubstituted C₃-C₁₀ cycloalkyl group, the substituted C₂-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀cycloalkenyl group, thesubstituted C₂-C₁₀ heterocycloalkenyl group, the substituted C₆-C₆₀ arylgroup, the substituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₇-C₆₀ arylalkyl group, the substitutedC₁-C₆₀ heteroaryl group, the substituted C₂-C₆₀ heteroarylalkyl group,the substituted monovalent non-aromatic condensed polycyclic group, andthe substituted monovalent non-aromatic condensed heteropolycyclic groupis: deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂,a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, or a C₁-C₆₀ alkoxy group; aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, or aC₁-C₆₀ alkoxy group, each substituted with deuterium, —F, —Cl, —Br, —I,—CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group,a nitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₇-C₆₀arylalkyl group, a C₁-C₆₀ heteroaryl group, a C₂-C₆₀ heteroarylalkylgroup, a monovalent non-aromatic condensed polycyclic group, amonovalent non-aromatic condensed heteropoly cyclic group, —N(Q₁₁)(Q₁₂),—Si(Q₁₃)(Q₁₄)(Q₁₅), —B(Q₁₆)(Q₁₇), —P(═O)(Q₁₈)(Q₁₉), or any combinationthereof; a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, aC₃-C₁₀ cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₇-C₆₀arylalkyl group, a C₁-C₆₀ heteroaryl group, C₂-C₆₀ heteroarylalkylgroup, a monovalent non-aromatic condensed polycyclic group, or amonovalent non-aromatic condensed heteropolycyclic group; a C₃-C₁₀cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₇-C₆₀ arylalkyl group, aC₁-C₆₀ heteroaryl group, C₂-C₆₀ heteroarylalkyl group, a monovalentnon-aromatic condensed polycyclic group, or a monovalent non-aromaticcondensed heteropolycyclic group, each substituted with deuterium, —F,—Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group,a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group,a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₇-C₆₀ arylalkyl group, a C₁-C₆₀ heteroarylgroup, C₂-C₆₀ heteroarylalkyl group, a monovalent non-aromatic condensedpolycyclic group, a monovalent non-aromatic condensed heteropoly cyclicgroup, —N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅), —B(Q₂₆)(Q₂₇), —P(═O)(Q₂₈)(Q₂₉),or any combination thereof; —N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅),—B(Q₃₆)(Q₃₇), or —P(═O)(Q₃₈)(Q₃₉); or any combination thereof, and Q₁ toQ₉, Q₁₁ to Q₁₉, Q₂₁ to Q₂₉, and Q₃₁ to Q₃₉ are each independentlyhydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryl groupsubstituted with a C₁-C₆₀ alkyl group, a C₆-C₆₀ aryl group, or anycombination thereof, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₇-C₆₀ arylalkyl group, a C₁-C₆₀ heteroaryl group, C₂-C₆₀heteroarylalkyl group, a monovalent non-aromatic condensed polycyclicgroup, or a monovalent non-aromatic condensed heteropoly cyclic group.2. The organometallic compound of claim 1, wherein R₁, R₂, R₄, R₅, R₂₁to R₂₉, and R_(10a) are each independently: hydrogen, deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, —SF₅, a C₁-C₂₀ alkylgroup, or a C₁-C₂₀ alkoxy group; a C₁-C₂₀ alkyl group or a C₁-C₂₀ alkoxygroup, each substituted with deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H,—CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptylgroup, a cyclooctyl group, an adamantyl group, a norbornenyl group, acyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, abicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, abicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a phenyl group,a biphenyl group, a terphenyl group, a naphthyl group, a pyridinylgroup, a pyrimidinyl group, or any combination thereof; a cyclopentylgroup, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, anadamantyl group, a norbornenyl group, a cyclopentenyl group, acyclohexenyl group, a cycloheptenyl group, a cyclooctenyl group, abicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, abicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a phenyl group,a biphenyl group, a terphenyl group, a naphthyl group, a fluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, an imidazopyridinyl group, or an imidazopyrimidinyl group, eachunsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD₃,—CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, acyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantylgroup, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group,a cycloheptenyl group, a cyclooctenyl group, a bicyclo[1.1.1]pentylgroup, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, abicyclo[2.2.2]octyl group, a phenyl group, a biphenyl group, a terphenylgroup, a naphthyl group, a fluorenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group,a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolylgroup, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, an isoindolyl group, an indolyl group, an indazolyl group, apurinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthrolinyl group, abenzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinylgroup, an imidazopyrimidinyl group, —Si(Q₃₃)(Q₃₄)(Q₃₅), or anycombination thereof; or —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇),—P(═O)(Q₈)(Q₉), or —P(Q₈)(Q₉), and Q₁ to Q₉ and Q₃₃ to Q₃₅ are eachindependently: —CH₃, —CD₃, —CD₂H, —CDH₂, —CH₂CH₃, —CH₂CD₃, —CH₂CD₂H,—CH₂CDH₂, —CHDCH₃, —CHDCD₂H, —CHDCDH₂, —CHDCD₃, —CD₂CD₃, —CD₂CD₂H, or—CD₂CDH₂; or an n-propyl group, an isopropyl group, an n-butyl group, anisobutyl group, a sec-butyl group, a tert-butyl group, an n-pentylgroup, an isopentyl group, a sec-pentyl group, a tert-pentyl group, aphenyl group, or a naphthyl group, each unsubstituted or substitutedwith deuterium, a C₁-C₁₀ alkyl group, a phenyl group, or any combinationthereof.
 3. The organometallic compound of claim 1, wherein R₁ and R₂are each independently: hydrogen, deuterium, —F, —Cl, —Br, —I, a cyanogroup, or —SF₅; or a methyl group, an ethyl group, a propyl group, ann-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group,an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentylgroup, an n-hexyl group, an isohexyl group, a sec-hexyl group, atert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptylgroup, a tert-heptyl group, an n-octyl group, an isooctyl group, asec-octyl group, a tert-octyl group, an n-nonanyl group, an isononanylgroup, a sec-nonanyl group, a tert-nonanyl group, an n-decanyl group, anisodecanyl group, a sec-decanyl group, a tert-decanyl group, a C₁-C₁₀alkoxy, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclooctyl group, an adamantyl group, a norbornyl group, a norbornenylgroup, a cyclopentenyl group, a cyclohexenyl group, or a cycloheptenylgroup, each unsubstituted or substituted with deuterium, —F, —Cl, —Br,—I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a cyano group, a C₁-C₂₀alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptylgroup, a cyclooctyl group, an adamantyl group, a norbornyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a biphenyl group, a naphthyl group,a pyridinyl group, a pyrimidinyl group, or any combination thereof, anda1 is an integer from 0 to
 5. 4. The organometallic compound of claim 1,wherein a group represented by

is one of Formulae 10-13(1) to 10-13(18) or 10-13:

wherein, in Formulae 10-13(1) to 10-13(18) and 10-13, R_(1a) to R_(1e)are each independently the same as defined in connection with R₁ inclaim 1, wherein R_(1a) to R_(1e) are each not hydrogen, and * indicatesa binding site to a neighboring carbon atom.
 5. The organometalliccompound of claim 1, wherein a group represented by

in Formula 2 is a group represented by one of Formulae CY21(1) toCY21(56):

wherein, in Formulae CY21(1) to CY21(56), X₂₁ and R₂₁ are eachindependently the same as described in claim 1, R_(21a) to R_(21d) areeach independently the same as defined in connection with R₂₁ in claim1, wherein R₂₁ and R_(21a) to R_(21d) are each not hydrogen, *″indicates a binding site to a carbon atom of a neighboring 6-memberedring in Formula 2, and * indicates a binding site to M in Formula
 1. 6.The organometallic compound of claim 1, wherein L₁ is a ligandrepresented by Formula 2A or 2B:

wherein, in Formulae 2A and 2B, X₁, X₂₁, ring CY₁, ring CY₂₁, X₄, X₅,R₁, R₂, R₂₁, a1, a21, L₁₁, b11, *, and *′ are each independently thesame as described in claim 1, wherein X₂ and X₃ are each independentlyO, S, or Se.
 7. The organometallic compound of claim 1, wherein, inFormula 1, L₂ is a bidentate ligand linked to M of Formula 1 via O, S,N, C, P, Si, or As.
 8. The organometallic compound of claim 1, wherein,in Formula 1, L₂ is a bidentate ligand represented by Formula 3:

wherein, in Formula 3, X₃₁ and X₃₂ are each independently O; X₃₁ is Oand X₃₂ is N; or X₃₁ is N and X₃₂ is C,

indicates any atomic group linking X₃₁ and X₃₂ to each other, and * and*′ each indicate a binding site to M in Formula
 1. 9. The organometalliccompound of claim 1, wherein, in Formula 1, L₂ is a group represented byone of Formulae 3A to 3F:

wherein, in Formulae 3A to 3F, Y₁₃ is O, N, N(Z₁), P(Z₁)(Z₂), orAs(Z₁)(Z₂), Y₁₄ is O, N, N(Z₃), P(Z₃)(Z₄), or As(Z₃)(Z₄), T₁₁ is asingle bond, a double bond, *—C(Z₁₁)(Z₁₂)—*′, *—C(Z₁₁)═C(Z₁₂)—*′,*═C(Z₁)—*′, *—C(Z₁₁)=*′, *═C(Z₁)—C(Z₁₂)═C(Z₁₃)—*′,*—C(Z₁₁)═C(Z₁₂)—C(Z₁₃)=*′, *—N(Z₁₁)—*′, or a C₅-C₃₀ carbocyclic groupthat is unsubstituted or substituted with at least one Zn group, a11 isan integer from 1 to 10, Y₁₁ and Y₁₂ are each independently C or N, T₂₁is a single bond, a double bond, O, S, C(Z₁₁)(Z₁₂), Si(Z₁₁)(Z₁₂), orN(Z₁₁), ring CY₁₁ and ring CY₁₂ are each independently a C₅-C₃₀carbocyclic group or a C₂-C₃₀ heterocyclic group, A₁ is P or As, Z₁ toZ₄ and Zn to Z₁₃ are each independently the same as defined inconnection with R₂₁ in claim 1, d1 and d2 are each independently aninteger from 0 to 10, and * and *′ each indicate a binding site to M inFormula
 1. 10. The organometallic compound of claim 1, wherein, inFormula 1, L₂ is a group represented by one of Formulae 3-1(1) to3-1(66) or 3-1(301) to 3-1(309):

wherein, in Formulae 3-1(1) to 3-1(66) and 3-1(301) to 3-1(309), X₄₁ isO, S, N(Z₂₁), C(Z₂₁)(Z₂₂), or Si(Z₂₁)(Z₂₂), Z₁ to Z₄, Z_(1a), Z_(1b),Z_(1c), Z_(1d), Z_(2a), Z_(2b), Z_(2c), Z_(2d), Z₁₁ to Z₁₄, and Z₂₂ areeach independently the same as defined in connection with R₂₁ in claim1, d14 and d42 are each is an integer from 0 to 4, d26 is an integerfrom 0 to 6, and * and *′ each indicate a binding site to M inFormula
 1. 11. An organometallic compound represented by one ofCompounds 1 to 420:


12. An organic light-emitting device comprising: a first electrode; asecond electrode; and an organic layer disposed between the firstelectrode and the second electrode and comprising an emission layer,wherein the organic layer comprises at least one organometallic compoundof claim
 1. 13. The organic light-emitting device of claim 12, whereinthe first electrode is an anode, the second electrode is a cathode, theorganic layer further comprises a hole transport region disposed betweenthe first electrode and the emission layer and an electron transportregion disposed between the emission layer and the second electrode, thehole transport region comprises a hole injection layer, a hole transportlayer, an electron blocking layer, a buffer layer, or any combinationthereof, and the electron transport region comprises a hole blockinglayer, an electron transport layer, an electron injection layer, or anycombination thereof.
 14. The organic light-emitting device of claim 12,wherein the emission layer comprises the organometallic compound. 15.The organic light-emitting device of claim 8, wherein the emission layerfurther comprises a host, and an amount of the host is larger than anamount of the organometallic compound.
 16. A diagnostic compositioncomprising at least one organometallic compound of claim 1.